4-Chloro-2-fluorophenyl isocyanate → HCID 52933908, compound

HRID 1024475Notes

Reaction equation

HRID 1024475 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[CH3:12][CH:13]([CH3:36])[CH:14]([NH:19][C:20]([C:22]1[S:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)[N:26]=1)=[O:21])[C:15]([O:17][CH3:18])=[O:16]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:33][C:30]2[CH:31]=[CH:32][C:27]([C:25]3[N:26]=[C:22]([C:20]([NH:19][C@@H:14]([CH:13]([CH3:36])[CH3:12])[C:15]([O:17][CH3:18])=[O:16])=[O:21])[S:23][CH:24]=3)=[CH:28][CH:29]=2)=[C:4]([F:11])[CH:3]=1

Participants

3

Reactant 2

HCID 45582034-Chloro-2-fluorophenyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933908HCID 52933908, compound

Procedure

The title compound was synthesized analogous to Example 23, using 4-chloro-2-fluoro-1-isocyanatobenzene and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 9.281 (s, 1H), 8.824-8.796 (d, J=8.4 Hz, 1H), 8.703 (s, 1H), 8.330 (s, 1H), 8.227-8.168 (t, J=8.7, 9 Hz, 1H), 8.069-8.040 (d, J=8.7 Hz, 2H), 7.589-7.560 (s, J=8.7 Hz, 2H), 7.508-7.463 (d, J=2.1, 11.1 Hz, 1H), 7.268-7.238 (d, J=9 Hz, 1H), 4.395-4.343 (t, J=7.8 Hz, 1H), 3.700 (s, 3H), 2.341-2.273 (m, 1H), 1.000-0.953 (t, J=6.9, 7.2 Hz, 6H); MS (ESI) m/z 503 (M−H), 505 (M+H)+.

Sources & evidence

ORD record
ord-17c79943ce314770bbbcd9d5dd8f03b9
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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