2-Fluorophenyl isocyanate → HCID 178477460, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21](/[C:23](=[N:27]/[C@H:28]([CH:33]([CH3:35])[CH3:34])[C:29]([O:31][CH3:32])=[O:30])/[S:24][CH2:25][CH3:26])[O:20][N:19]=2)=[CH:14][CH:13]=1>>[CH2:25]([S:24]/[C:23](=[N:27]\[C@H:28]([CH:33]([CH3:34])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])/[C:21]1[O:20][N:19]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9]([NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[O:10])=[CH:13][CH:14]=2)[CH:22]=1)[CH3:26]Participants
3
Procedure
The title compound was prepared according to the procedure as set forth in example 151, except that 1-fluoro-2-isocyanatobenzene was used in place of 1-fluoro-3-isocyanatobenzene and (R,Z)-methyl 2-((3-(4-aminophenyl)isoxazol-5-yl)(ethylthio) methyleneamino)-3-methylbutanoate was used in place of methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate to yield 76% of the title compound. MS (ESI): m/z 499 (M+H)+; 1HNMR (DMSO-d6, 300 MHz): δ 8.124 (s, 1H), 8.101 (d, 1H), 7.858 (s, 1H), 7.593 (m, 1H), 7.406 (m, 1H), 7.260 (s, 2H), 7.095 (m, 2H), 6.991 (m, 1H), 6.701(d, 1H), 4.583 (d, 1H), 3.843 (s, 3H), 3.075 (m, 2H), 2.450 (s, 1H), 1.331 (t, 3H), 1.076 (d, 6H).