Unprecedented In Water Imidazole- Carbonylation: Paradigm shift for Preparation of Urea and Carbamate
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1 Unprecedented In Water Imidazole- Carbonylation: Paradigm shift for Preparation of Urea and Carbamate Kamlesh J. Padiya* Sandip Gavade, Bhavana Kardile, Manojkumar Tiwari, Swapnil Bajare, Madhav Mane, Vivek Gaware, Shaji Varghese, Dipak Harel, and Suresh Kurhade Department of Medicinal Chemistry Nycomed Pharma Pvt. Ltd , Suren Road, Andheri east, Mumbai 4 93, Maharashtra, India Table of Contents 1. General Information 2 2. General experimental procedure for imidazole-carbonylation of amine General experimental procedure for preparation of Urea / Carbamates / Thiocarbamates. imidazole-carbonylation of amine 3 4. Copies of 1 H NMR spectra Copies of mass spectra
2 General Information: All reactions were run in the air with magnetic stirring. All the reaction were carried out in tap water (ph was measured between 6. to 6.5). Use of deionized water did not added any advantage to reactions in terms of yield or separation of product formed. All reagents were purchased from commercial suppliers and used without further purification. rganic solutions were concentrated under reduced pressure on a Heidolph rotary evaporator. Reactions were monitored by thin layer chromatography on silica gel precoated aluminium plates (Merck, TLC silica gel 6 F254). UV light at 254 nm or KMn4 stains were used to visualize TLC plates. Flash column chromatography from Combiflash companion was used for purification of compound 1h, when prepared using solvent other than water. Chemical yields refer to pure isolated substances unless stated otherwise. 1H-NMR spectra were recorded on a Bruker 3 spectrometer and the chemical shifts are reported in ppm relative to tetramethylsilane with the solvent resonance as the internal standard. Liquid chromatography tandem mass spectrometry (LC/MS/MS) were performed on a Thermo-Finnigan Accela UHPLC system. The system was equipped with auto sampler, Accela pump, Photo diode array detector using Waters Acquity BEH C18 (5 x 2.1 mm X 1.7 micron) column. System was interfaced with a Thermo Finnigan LCQ Advantage Max ion trap mass spectrometer via an ESI probe. All data were collected in the positive ion mode. Instrument parameters were: heated capillary, 32 C; sheath gas (N2), 55; auxiliary gas (N2), 15; total two micro scans; maximum injection time, 2 ms. For MS experiments, the mass range scanned was m/z 5 9. MS/MS parameters were: IW 1.; RCE 4%. General Procedure for preparation of Carbonylimidazolide of amine : Amine (1 mmol) was taken in water and stirred at C. CDI (1.2 mmol) was added in reaction mixture at C. Reaction mixture was stirred at C for 1 hr and then warm upto room temperature. Reaction was monitored with TLC. Complete conversion was observed within 2 min for most of the amine. In most cases product gets precipitated out in aqueous solution. Reaction mixture was filtered; precipitate obtained was washed with cold water and dried. In case if there s no precipitation of product Reaction mixture was extracted with 3 to 4 times by ethyl acetate. rganic layer was washed thrice with water, dried over sodium sulphate, evaporated in vacuu, and purified by column chromatography 2
3 General Procedure for preparation of Urea / Carbamate / Thiocarbamate:- Amine (1 mmol) was taken in water at room temperature and stirred at C. CDI (1.2 mmol) was added in reaction mixture at C. Reaction mixture was stirred at C for 1 hr and then warm upto room temperature. Reaction was monitored with TLC. After complete formation of carbonylimidazolide, nucleophile (R-NH 2 / R-H / R-SH) (1.2 mmol) was added. Reaction mixture was stirred at room temperature and monitored by TLC. In most cases complete conversion was observed within 2 h. Reaction mixture was filtered; precipitate obtained was washed with cold water and dried. In case if there s no precipitation of product, reaction mixture was extracted with 3 to 4 times by ethyl acetate. rganic layer was washed thrice with water, dried over sodium sulphate, evaporated in vacuu, and purified by column chromatography. 3
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5 1H NMR (DMS-d 6,3MHz): δ = 9.16 (t, J=5.9 Hz, 1 H), 8.28 (s, 1 H), (m, 2 H), 7.7 (s, 1 H), 7.48 (d, J=8.5 Hz, 2 H), 7.4 (s, 1 H), 4.54 (d, J=5.9 Hz, 2 H), 4.29 (q, J=7.2 Hz, 2 H), 1.3 ppm (t, J=7.2 Hz, 3 H) Date 12 Jan 28 7:4:32 Comment 11272/MUKJP/56/1 Solvent DMS-d6 1. i81123_1fid H 3 C NH N N 1a
6 1H NMR (CHLRFRM-d,3MHz): δ = 8.7 (t, 1 H), (m, 6 H), (m, 1 H), 6.7 (br. s., 1 H), 4.59 ppm (d, J=5.7 Hz, 2 H) Date 1 Jan 28 11:5:24 Comment 11273/MUKJP/21/1 Solvent CHLRFRM-d 1..9 i8113_28fid N NH N 1b
7 Date 14 Jan 28 4:35:12 Comment 11227/MUKJP/234/1 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 1.17 (br. s., 1 H), 8.38 (s, 1 H), 7.82 (s, 1 H), 7.25 (br. s., 1 H), (m, 2 H), 6.98 (d, J=8.7 Hz, 1 H), 3.76 ppm (s, 6 H) i81143_1fid N NH N 1c
8 Date 11 Jan 28 7:8:48 Comment 11227/MUKJP/235/1 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 1.17 (s, 1 H), 8.37 (s, 1 H), 7.81 (s, 1 H), 7.51 (d, J=9.1 Hz, 2 H), 7.9 (s, 1 H), 6.98 (d, J=9.1 Hz, 2 H), 3.76 ppm (s, 3 H).4 i81113_19fid N NH N 1d
9 1H NMR (DMS-d 6,3MHz): δ = 8. (t, J=1.1 Hz, 1 H), 7.44 (t, J=1.5 Hz, 1 H), 7.2 (t, J=1.3 Hz, 1 H), (m, 4 H), ppm (m, 7 H) Date 11 Jan 28 5:2: Comment 11246/MUKJP/168/1 Solvent DMS-d6 1. i81113_9fid N N 1e N
10 Date 11 Jan 28 5:15:44 Comment 11246/MUKJP/167/1 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 7.62 (t, J=.9 Hz, 1 H), (m, 2 H), (m, 3 H), (m, 1 H), (m, 1 H), 3.4 ppm (s, 3 H) 1f.esp N N N 1f
11 Date 21 Nov 27 7:51:28 Comment 1733/MUKJP/119/31 Solvent CHLRFRM-d 1H NMR (CHLRFRM-d,3MHz): δ = 7.89 (d, J=1.1 Hz, 1 H), 7.23 (t, J=1.5 Hz, 1 H), (m, 1 H), 3.45 (q, J=7.2 Hz, 4 H), 1.27 ppm (t, J=7.2 Hz, 6 H) 1g.esp N N N 1g
12 1H NMR (DMS-d 6,3MHz): δ = 8.9 (t, J=.8 Hz, 1 H), 7.54 (t, J=1.3 Hz, 1 H), 7.2 (s, 4 H), 7.5 (t, 1 H), (m, 1 H), 4.69 (s, 2 H), 3.68 (t, J=5.9 Hz, 2 H), 2.93 ppm (t, J=5.9 Hz, 2 H) Date 7 Nov 27 6:38:56 Comment 1733/MUKJP/19/1 Solvent DMS-d6 1. i71173_8fid N N N 1h
13 1H NMR (DMS-d 6,3MHz): δ = 7.9 (d, J=8.3 Hz, 2 H), 7.4 (d, J=8.7 Hz, 2 H), 7.26 (t, J=5.9 Hz, 1 H), (m, 4 H), 4.53 (s, 2 H), (m, 4 H), 3.6 (t, J=6. Hz, 2 H), 2.79 (t, J=5.9 Hz, 2 H), 1.31 ppm (t, J=7. Hz, 3 H) Date 24 Mar 28 6:9:4 Comment 11272MUKJP79/11 Solvent DMS-d6 2a.esp NH N 2a
14 1H NMR (DMS-d 6,3MHz): δ = 8.57 (s, 1 H), 8.2 (d, J=2.6 Hz, 1 H), 7.78 (dd, J=8.7, 2.6 Hz, 1 H), 7.19 (s, 4 H), 6.74 (d, J=8.7 Hz, 1 H), 4.63 (s, 2 H), 3.8 (s, 3 H), 3.69 (t, J=5.9 Hz, 2 H), 2.85 ppm (t, J=5.9 Hz, 2 H) Date 16 Jan 28 6:58:8 Comment 1733/MUKJP/216/1 Solvent DMS-d6 i81163_17fid NH N N 2b
15 1H NMR (DMS-d 6,3MHz): δ = 8.5 (s, 1 H), 8.16 (d, J=2.6 Hz, 1 H), 7.74 (dd, J=8.7, 2.6 Hz, 1 H), 6.73 (d, J=8.7 Hz, 1 H), 3.78 (s, 3 H), (m, 5 H), (m, 4 H), ppm (m, 5 H) Date 31 ct 27 5:41:2 Comment 1733/MUKJP/13/1 Solvent DMS-d6 i71313_1fid NH N N 2c
16 Date 15 Jan 28 1:54:56 Comment 11273/MUKJP/22/11 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = (m, 4 H), (m, 6 H), 4.53 (s, 2 H), 4.27 (d, J=5.7 Hz, 2 H), 3.59 (t, J=6. Hz, 2 H), 2.78 ppm (t, J=6. Hz, 2 H).7 2d.esp NH N 2d
17 1H NMR (DMS-d 6,3MHz): δ = (m, 2 H), (m, 8 H), 6.54 (t, J=5.9 Hz, 1 H), 4.22 (d, J=5.7 Hz, 2 H), 3.18 ppm (s, 3 H) Date 17 Jan 28 11:1:2 Comment 11273/MUKJP/23/1 Solvent DMS-d6 i81173_25fid NH N 2e
18 1H NMR (DMS-d 6,3MHz): δ = (m, 5 H), 7.1 (t, J=5.9 Hz, 1 H), 4.25 (d, J=6. Hz, 2 H), (m, 4 H), ppm (m, 4 H) Date 16 Jan 28 11:58:56 Comment 11273/MUKJP/27/1 Solvent DMS-d6.55 2f.esp f NH N
19 1H NMR (DMS-d 6,3MHz): δ = 8.53 (s, 1 H), 8.48 (s, 1 H), 8.17 (d, J=2.3 Hz, 1 H), 7.82 (dd, J=8.9, 2.8 Hz, 1 H), 7.18 (s, 1 H), 6.86 (s, 2 H), 6.77 (d, J=8.7 Hz, 1 H), 3.81 (s, 3 H), 3.73 (s, 3 H), 3.7 ppm (s, 3 H) Date 18 Jan 28 5:34:56 Comment 11227/MUKJP/24/5 Solvent DMS-d6.4 2g.esp NH NH N 2g
20 Date 18 Jan 28 6:53:52 Comment 11266/MUKJP/17/1 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 8.3 (s, 1 H), 7.27 (d, J=9.1 Hz, 2 H), 6.8 (d, J=9.1 Hz, 2 H), 6.7 (t, J=5.5 Hz, 1 H), 3.69 (s, 3 H), (m, 4 H), 3.27 ppm (s, 3 H) i81183_19fid NH NH 2h
21 Date 18 Jan 28 6:58:8 Comment 11266/MUKJP/18/1 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = (m, 2 H), (m, 4 H), 5.87 (t, J=5.5 Hz, 1 H), (m, 2 H), 3.21 (s, 3 H), (m, 2 H), 3.14 ppm (s, 3 H) 2i.esp NH N 2i
22 1H NMR (DMS-d 6,3MHz): δ = (m, 5 H), 6.39 (t, J=5.9 Hz, 1 H), 5.98 (t, J=5.5 Hz, 1 H), 4.2 (d, J=6. Hz, 2 H), 3.33 (s, 2 H), 3.25 (s, 3 H), 3.18 ppm (q, J=5.5 Hz, 2 H) Date 18 Jan 28 7:4:32 Comment 11266/MUKJP/19/1 Solvent DMS-d6 2j.esp NH NH CH 3 2j
23 1H NMR (DMS-d 6,3MHz): δ = 8.21 (s, 1 H), (m, 4 H), (m, 2 H), (m, 1 H), (m, 2 H), 3.26 ppm (s, 3 H) Date 24 Jan 28 7:8:48 Comment 11246/MUKJP/181/5 Solvent DMS-d6 2k.esp CH3 NH N F 2k
24 1H NMR (DMS-d 6,3MHz): δ = 8.6 (s, 1 H), 8.45 (s, 1 H), 7.45 (dd, J=9.1, 4.9 Hz, 2 H), 7.35 (d, J=9.1 Hz, 2 H), 7.1 (t, J=8.9 Hz, 2 H), 6.87 (d, J=8.7 Hz, 2 H), 3.71 ppm (s, 3 H) Date 22 Jan 28 5:28:32 Comment 11246/MUKJP/181/1 Solvent DMS-d6 i81223_6fid NH NH F CH3 2l
25 Date 22 Jan 28 9:4:16 Comment 11246/MUKJP/181/3 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 8.54 (s, 1 H), 7.37 (dd, J=9.3, 5.1 Hz, 2 H), 7.5 (t, J=9.1 Hz, 2 H), 6.16 (t, J=5.5 Hz, 1 H), (m, 5 H), ppm (m, 2 H) i81223_27fid NH NH CH 3 F 2m
26 Date 23 Jan 28 8:53:2 Comment 11246/MUKJP/181/6 Solvent DMS-d6 1H NMR (DMS-d 6,3MHz): δ = 8.61 (s, 1 H), (m, 2 H), 7.19 (s, 4 H), 7.8 (t, 2 H), 4.63 (s, 2 H), 3.69 (t, J=5.9 Hz, 2 H), 2.85 ppm (t, J=6. Hz, 2 H) 1. i81233_22fid NH N F 2n
27 1H NMR (DMS-d 6,3MHz): δ = 8.4 (s, 1 H), 7.18 (s, 5 H), 7. (d, J=8.7 Hz, 1 H), 6.83 (d, J=8.7 Hz, 1 H), 4.62 (s, 2 H), 3.7 (d, J=4.2 Hz, 8 H), 2.84 ppm (t, J=5.9 Hz, 2 H) Date 18 Jan 28 5:2: Comment 11227/MUKJP/24/1 Solvent DMS-d6.4 2o.esp H3C NH N H3C 2o
28 1H NMR (DMS-d 6,3MHz): δ = 8.34 (s, 1 H), 7.15 (d, J=2.3 Hz, 1 H), (m, 2 H), (m, 1 H), 3.7 (s, 4 H), 3.68 (s, 3 H), 3.36 (s, 2 H), 3.27 (s, 3 H), ppm (m, 2 H) Date 17 Jan 28 6:38:56 Comment 11227/MUKJP/24/4 Solvent DMS-d6 2p.esp H 3 C NH NH CH 3 H 3 C 2p
29 1H NMR (DMS-d 6,3MHz): δ = (m, 4 H), 6.59 (t, J=5.5 Hz, 1 H), 4.47 (s, 2 H), 3.53 (t, J=5.9 Hz, 2 H), (m, 2 H), 3.24 (s, 3 H), (m, 2 H), 2.75 ppm (t, J=5.9 Hz, 2 H) Date 18 Jan 28 7:8:48 Comment 11266/MUKJP/11/1 Solvent DMS-d6 2q.esp N NH CH 3 2q
30 1H NMR (DMS-d 6,3MHz): δ = 8.47 (s, 1 H), 8.13 (d, J=3. Hz, 1 H), 7.77 (dd, J=8.7, 2.6 Hz, 1 H), (m, 5 H), 6.72 (d, J=8.7 Hz, 1 H), 6.64 (t, J=6. Hz, 1 H), 4.28 (d, J=5.7 Hz, 2 H), 3.77 ppm (s, 3 H) Date 11 Feb 28 5:13:36 Comment 1733/MUKJP/242/11 Solvent DMS-d6 i82113_3fid NH NH N 2r
31 1H NMR (DMS-d 6,3MHz): δ = 7.9 (d, J=8.3 Hz, 2 H), (m, 4 H), (m, 3 H), 6.67 (t, J=5.9 Hz, 1 H), (m, 4 H), 3.34 (s, 3 H), 1.31 ppm (t, J=7.2 Hz, 3 H) Date 12 Mar 28 4:5:2 Comment 11272MUKJP8/11 Solvent DMS-d6 1. 2s.esp NH N H3C CH3 2s
32 1H NMR (DMS-d 6,3MHz): δ = 8.43 (s, 1 H), 7.93 (d, J=8.3 Hz, 2 H), 7.43 (d, J=8.3 Hz, 2 H), (m, 2 H), (m, 2 H), 6.61 (t, J=6. Hz, 1 H), (m, 2 H), (m, 2 H), 3.69 (s, 3 H), 1.32 ppm (t, J=7.2 Hz, 4 H) Date 13 Mar 28 11:5:36 Comment 11272MUKJP84/11 Solvent DMS-d6.8 i83133_27fid CH 3 NH NH 2t
33 1H NMR (DMS-d 6,3MHz): δ = 1.13 (s, 1 H), 8.27 (s, 1 H), 7.81 (dd, J=8.9, 2.8 Hz, 1 H), 7.14 (d, J=9.1 Hz, 2 H), 6.95 (d, J=9.4 Hz, 2 H), 6.82 (d, J=9.1 Hz, 1 H), 3.81 (s, 3 H), 3.76 ppm (s, 3 H) Date 21 Jan 28 4:48: Comment 1733/MUKJP/218/11 Solvent DMS-d6 1. i81213_4fid NH N 3a
34 1H NMR (DMS-d 6,3MHz): δ = 8.32 (t, J=6.2 Hz, 1 H), 7.96 (d, J=8.3 Hz, 2 H), 7.46 (d, J=8.3 Hz, 2 H), 7.5 (d, 2 H), 6.91 (d, J=9.1 Hz, 2 H), (m, 4 H), 3.74 (s, 3 H), 1.33 ppm (t, J=7.2 Hz, 2 H) Date 24 Mar 28 5:52: Comment 11272MUKJP92/21 Solvent DMS-d6 1. i83243_12fid NH 3b
35 1H NMR (DMS-d 6,3MHz): δ = 1.21 (br. s., 1 H), 8.28 (d, J=2.3 Hz, 1 H), 7.81 (dd, J=8.9, 2.8 Hz, 1 H), (m, 3 H), 6.98 (t, J=8.9 Hz, 1 H), (m, 1 H), 6.73 (dd, J=9.1, 4.5 Hz, 1 H), ppm (m, 3 H) Date 11 Feb 28 12:24:32 Comment 1733/MUKJP/243/1 Solvent DMS-d6 1. i82113_29fid NH N 3c
36 1H NMR (DMS-d 6,3MHz): δ = 1.19 (br. s., 1 H), 8.28 (d, J=2.6 Hz, 1 H), 7.82 (dd, J=8.7, 2.6 Hz, 1 H), 7.43 (t, 2 H), (m, 3 H), 6.83 (d, J=8.3 Hz, 1 H), 3.82 ppm (s, 3 H) Date 11 Feb 28 12:2:16 Comment 1733/MUKJP/244/1 Solvent DMS-d6 3. NH N F 3d i82113_28fid
37 1H NMR (DMS-d 6,3MHz): δ = 1.2 (br. s., 1 H), 7.51 (dd, J=9.1, 4.9 Hz, 2 H), (m, 4 H), 6.95 (d, J=9.1 Hz, 2 H), 3.76 ppm (s, 3 H) Date 7 Mar 28 14:21:52 Comment 11246MUKJP227/1 Solvent DMS-d6 i8373_23fid NH F 3e
38 1H NMR (DMS-d 6,3MHz): δ = 1.27 (br. s., 1 H), 7.52 (dd, J=9.1, 4.9 Hz, 2 H), (m, 2 H), ppm (m, 5 H) NH Date 25 Feb 28 7:55:44 Comment 11246/MUKJP/27/21 Solvent DMS-d6 F 3f 1. i82253_32fid
39 1H NMR (DMS-d 6,3MHz): δ = 1.29 (br. s., 1 H), 7.51 (dd, J=9.1, 4.9 Hz, 2 H), (m, 4 H), 7.18 ppm (t, J=8.9 Hz, 2 H) NH Date 25 Feb 28 7:51:28 Comment 11246/MUKJP/27/22 Solvent DMS-d6 F F 3g 1. i82253_31fid
40 Date 27 Feb 28 8:55:28 Comment 11266MUKJP134/11 Solvent CHLRFRM-d 1H NMR (CHLRFRM-d,3MHz): δ = (m, 2 H), (m, 3 H), 5.4 (br. s., 1 H), (m, 2 H), (m, 2 H), 3.41 ppm (s, 3 H) 1. i82273_18fid NH 3h
41 1H NMR (CHLRFRM-d,3MHz): δ = 7.4 (d, J=9.4 Hz, 2 H), 6.86 (d, J=9.1 Hz, 2 H), (m, 1 H), 3.79 (s, 3 H), (m, 2 H), 3.46 (t, J=5.5 Hz, 2 H), 3.4 ppm (s, 3 H) Date 27 Feb 28 8:49:4 Comment 11266MUKJP135/11 Solvent CHLRFRM-d i82273_17fid NH 3i
42 1H NMR (CHLRFRM-d,3MHz): δ = (m, 4 H), 5.41 (br. s., 1 H), (m, 2 H), 3.46 (t, J=5.5 Hz, 2 H), 3.4 ppm (s, 3 H) Date 27 Feb 28 8:44:48 Comment 11266MUKJP136/11 Solvent CHLRFRM-d i82273_16fid NH F 3j
43 1H NMR (DMS-d 6,3MHz): δ = 1.54 (br. s., 1 H), 8.29 (d, J=2.3 Hz, 1 H), 7.79 (dd, J=9.1, 2.6 Hz, 1 H), (m, 2 H), (m, 3 H), 6.81 (d, J=8.7 Hz, 1 H), 3.81 ppm (s, 3 H) Date 21 Jan 28 4:52:16 Comment 1733/MUKJP/219/11 Solvent DMS-d6 1. i81213_5fid NH S H 3 C N 4a
44 1H NMR (DMS-d 6,3MHz): δ = 1.35 (s, 1 H), (m, 2 H), (m, 3 H), 7.21 (d, J=2.3 Hz, 1 H), (m, 1 H), (m, 1 H), 3.71 ppm (d, J=3. Hz, 6 H) Date 17 Jan 28 6:43:12 Comment 11227/MUKJP/24/6 Solvent DMS-d6 1. i81173_14fid H 3 C NH S H 3 C 4b
45 NH S Date 23 Jan 28 6:13:2 Comment 11246/MUKJP/181/4 Solvent DMS-d6 F 4c 1H NMR (DMS-d 6,3MHz): δ = 1.57 (s, 1 H), (m, 4 H), (m, 3 H), ppm (m, 2 H) 1. i81233_14fid
46 1H NMR (CHLRFRM-d,3MHz): δ = 7.58 (dd, J=6.6, 3.2 Hz, 2 H), (m, 3 H), 5.75 (br. s., 1 H), 3.46 (s, 4 H), 3.34 ppm (s, 3 H) H3C NH S Date 13 Mar 28 11:22:4 Comment 11266MUKJP147/1 Solvent CHLRFRM-d 4d 1. i83133_29fid
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