2,4-Difluorophenyl isocyanate → (S)-methyl 2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoate

HRID 75856노트

반응식

HRID 75856 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:15][C@@H:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[N:32]=[C:33]=[O:34]>C1COCC1>[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[NH:32][C:33](=[O:34])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:15][C@@H:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[N:12]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 67352540(S)-methyl 2-(2-(4-aminophenyl)thiazole-4-carboxamido)-3-methylbutanoate

생성물 1

HCID 67352417(S)-methyl 2-(2-(4-(3-(2,4-difluorophenyl)ureido)phenyl)thiazole-4-carboxamido)-3-methylbutanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(S)-methyl 2-(2-(4-aminophenyl)thiazole-4-carboxamido)-3-methylbutanoate (150 mg, 0.450 mmol) was taken in 3 mL THF, to this 2,4-difluoro-1-isocyanatobenzene (76.8 mg, 0.495 mol) was added and stirred at RT for 3-4 hr. After completion of reaction solvent was removed under reduced pressure and the residue purified by column chromatography. Yield: 200 mg (91%). MS (ESI) m/z: 487(M−H)−; 1HNMR (DMSO-d6, 300 MHz): δ 9.369 (s, 1H), 8.594 (d, 1H), 8.316 (s, 1H), 8.291 (s, 1H), 8.126 (m, 1H), 8.023 (d, 2H), 7.640 (d, 2H), 7.372 (m, 1H), 7.106 (m, 1H), 4.431 (dd, 1H), 3.696 (s, 3H), 2.300 (m, 1H), 0.981 (dd, 6H).

후처리

  1. additionwas added
  2. customAfter completion of reaction solvent
  3. customwas removed under reduced pressure
  4. customthe residue purified by column chromatography

출처 및 근거

ORD 기록
ord-0def355d1c7e43f39507811fec355f7e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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