Ammonia → (S)-5-Methyl-3-phenyl-2-(1-((5-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052779노트

반응식

HRID 1052779 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:13]([NH:15][C@H:16]([C:18]4[N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:22](=[O:30])[C:21]5=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]5[N:19]=4)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=3[N:8](COCC[Si](C)(C)C)[CH:7]=2)=[N:2]1.[F:43][C:44]([F:48])([F:47])[CH2:45]I.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)C(O)=O.N>CN(C=O)C>[CH3:34][C:31]1[CH:32]=[CH:33][N:20]2[C:21]=1[C:22](=[O:30])[N:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]([C@@H:16]([NH:15][C:13]1[C:14]3[C:6]([C:3]4[CH:4]=[CH:5][N:1]([CH2:45][C:44]([F:48])([F:47])[F:43])[N:2]=4)=[CH:7][NH:8][C:9]=3[N:10]=[CH:11][N:12]=1)[CH3:17])=[N:19]2

참가 물질

7

반응물 5

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 178428095HCID 178428095, 화합물

생성물 1

HCID 136623660(S)-5-Methyl-3-phenyl-2-(1-((5-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one수율 12.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

(S)-2-(1-((5-(1H-Pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.07 mmol) and 1,1,1-trifluoro-2-iodoethane (36 mg, 0.17 mmol) were dissolved in DMF (2 ml) and cesium carbonate (140 mg, 0.43 mmol) was added. After stirring the mixture at 80° C. for 2 h, the solvent was evaporated under reduced pressure and the residue was suspended in water and extracted with ethyl acetate (×3). The organic phase was successively washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. The residue (54 mg) was treated with trifluoroacetic acid (1 mL, 13 mmol) and a solution of ammonia (7N in methanol, 10 ml, 70 mmol) according to the method described in Example 27 to give 4.6 mg (12% yield) of the title compound. Purity 93%.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic phase was successively washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-4e66e3cd75524883a75ad8a9617e14a1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

반응 노트

불러오는 중…