2-Fluorophenyl isocyanate → HCID 67354286, compound

HRID 75825

Reaction equation

HRID 75825 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]([NH:25][CH:26]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:27]([O:29][CH3:30])=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][CH:13]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:10])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([NH:25][CH:26]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:27]([O:29][CH3:30])=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 67355008Methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-phenylpropanoate

Product 1

HCID 67354286HCID 67354286, compoundYield 88%

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 methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-phenylpropanoate was used in place of methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate to yield 88% of the title compound. MS (ESI): m/z 503.2 (M+H)+; 1HNMR (DMSO-d6, 300 MHz): δ 9.43 (d, 1H), 9.33 (s, 1H), 8.63 (s, 1H), 8.16 (dt, 1H), 7.84 (d, 2H), 7.61 (d, 2H), 7.56 (s, 1H), 7.27 (d, 4H), 7.23 (m, 2H), 7.15 (t, 1H), 7.00 (m, 1H), 4.74 (m, 1H), 3.65 (s, 3H), 3.23 (m, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-719b4d9698e34c2993654d4bed0cc8b8
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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