2,4-Difluorophenyl isocyanate → Methyl 2-(3-(4-(3-(2,4-difluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-phenylpropanoate

HRID 75826Notes

Reaction equation

HRID 75826 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:23]=[C:22]([C:24]([NH:26][CH:27]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:28]([O:30][CH3:31])=[O:29])=[O:25])[O:21][N:20]=2)=[CH:15][CH:14]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:11])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:23]=[C:22]([C:24]([NH:26][CH:27]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:28]([O:30][CH3:31])=[O:29])=[O:25])[O:21][N:20]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 67355008Methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-phenylpropanoate

Product 1

HCID 67354042Methyl 2-(3-(4-(3-(2,4-difluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-phenylpropanoateYield 62%

Procedure

The title compound was prepared according to the procedure as set forth in example 151, except that 2,4-difluoro-1-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 62% of title compound. MS (ESI): m/z 521.2 (M+H)+; 1HNMR (DMSO-d6, 300 MHz) δ: 9.43(d, 1H), 9.28 (s, 1H), 8.58(s, 1H), 8.10 (m, 1H), 7.84 (d, 2H), 7.60 (d, 2H), 7.55 (s, 1H), 7.34 (m, 5H), 7.20 (m, 1H), 7.07 (m, 1H), 4.74 (m. 1H), 3.64 (s, 3H), 3.23 (m, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cfdff0c4fdc6405d869529a5653698f5
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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