4-Chloro-6-(trifluoromethyl)pyrimidine → (S)-tert-butyl 2-(2-fluoro-4-(1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

HRID 571886노트

반응식

HRID 571886 반응식
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][NH:14][CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C@@H:16]1[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.Cl[C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[CH:32][N:31]=1>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[CH:32][N:31]=3)[CH:15]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[C@@H:16]1[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1

참가 물질

4

반응물 2

HCID 115428814-Chloro-6-(trifluoromethyl)pyrimidineHCID 71087137(S)-tert-butyl 2-(2-fluoro-4-(1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

생성물 1

HCID 71087182(S)-tert-butyl 2-(2-fluoro-4-(1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

Under N2, (S)-tert-butyl 2-(2-fluoro-4-(1H-pyrazole-4-carboxamido)phenyl)morpholine-4-carboxylate (60 mg, 154 μmol, Eq: 1.00), 4-chloro-6-(trifluoromethyl)-pyrimidine (CAS 37552-81-1) (28 mg, 154 μmol, Eq: 1.00) and were combined in DMSO (2 ml). The orange solution was stirred at 120° C. over 1 hour. Control with TLC: the reaction was finished. At RT, the RM was partitioned between water and EtOAc; extracted; the organic layer was washed with water and brine; dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 15% to 60% EtOAc in heptane). Yellow solid (41 mg). MS: 535.7 ([M−H]−)

후처리

  1. customAt RT, the RM was partitioned between water and EtOAc
  2. extractionextracted
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 10 g, 15% to 60% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-f134b766870b431ebb437ef8aba72f6b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029370B2

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