4-Chlorophenyl Isocyanate → HCID 52933174, compound

HRID 1024468Notes

Reaction equation

HRID 1024468 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH3:11][CH:12]([CH3:35])[CH:13]([NH:18][C:19]([C:21]1[S:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)=[CH:24][N:25]=1)=[O:20])[C:14]([O:16][CH3:17])=[O:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:32][C:29]2[CH:30]=[CH:31][C:26]([C:23]3[S:22][C:21]([C:19]([NH:18][C@@H:13]([CH:12]([CH3:35])[CH3:11])[C:14]([O:16][CH3:17])=[O:15])=[O:20])=[N:25][CH:24]=3)=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933174HCID 52933174, compound

Procedure

The title compound was synthesized analogous to Example 9, using 1-chloro-4-isocyanatobenzene and intermediate 2. 1HNMR (DMSO-d6, 300 MHz): δ 8.991 (s, 1H), 8.897 (s, 1H), 8.737-8.710 (d, 1H), 8.353 (s, 1H), 7.730-7.701 (d, J=8.7 Hz, 2H), 7.583-7.554 (d, J=8.7 Hz, 2H), 7.513-7.484 (d, J=8.7 Hz, 2H), 7.355-7.325 (d, J=9 Hz, 2H), 4.324-4.287 (t, J=7.2, 7.8 Hz, 1H), 3.681 (s, 3H), 2.342-2.242 (m, 1H), 0.965-0.923 (d, J=6.3 Hz, 6H); MS (ESI) m/z 487 (M+H)+.

Sources & evidence

ORD record
ord-70a0ad99300647a8a5822d1711c2ffd2
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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