3-Fluorophenyl isocyanate → Methyl 2-(3-(4-(3-(3-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

HRID 75821

반응식

HRID 75821 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]=[C:32]=[O:33])[CH:26]=1>C1COCC1>[F:24][C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:33])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=3)=[CH:4][CH:3]=2)[CH:28]=[CH:29][CH:30]=1

참가 물질

4

반응물 2

HCID 1230643-Fluorophenyl isocyanateHCID 67352790Methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate

생성물 1

HCID 67353251Methyl 2-(3-(4-(3-(3-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate수율 64.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate (500 mg) dissolved in THF (10 ml) was added 1-fluoro-3-isocyanatobenzene (260 mg) and stirred at RT overnight. The solid was filtered and washed with THF to yield 460 mg (64%) white solid. MS (ES+): m/z 455 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ 9.19 (d, 1H), 9.16 (s, 1H), 9.13 (s, 1H), 7.84 (d, 2H), 7.67 (s, 1H), 7.62 (d, 2H), 7.5 (dd, 1H), 7.31 (m, 1H), 7.13 (dd, 1H), 6.78 (m, 1H), 4.29 (m, 1H), 3.66 (s, 3H), 2.2 (m, 1H), 0.95 (d, 6H).

후처리

  1. filtrationThe solid was filtered
  2. washwashed with THF

출처 및 근거

ORD 기록
ord-015dc18f1a4545b0be771c903d953dab
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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