Cesium carbonate → (S)-2-(1-((5-(1-(2-Hydroxyethyl)-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

HRID 1052586노트

반응식

HRID 1052586 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]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:7]=2)=[N:2]1.Br[CH2:44][CH2:45][OH:46].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[OH:46][CH2:45][CH2:44][N: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:25]=[CH:26][CH:27]=[CH:28][CH:29]=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]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:42])[CH3:41])[CH:7]=2)=[N:2]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 178428095HCID 178428095, 화합물

생성물 1

HCID 131736211(S)-2-(1-((5-(1-(2-Hydroxyethyl)-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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °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 (38 mg, 0.07 mmol) and 2-bromoethanol (15 mg, 0.12 mmol) were dissolved in DMF (1.5 ml) and cesium carbonate (102 mg, 0.31 mmol) was added. After stirring the mixture at 75° C. for 2 h, the solvent was evaporated under reduced pressure and the residue was suspended in water, basified with sodium carbonate 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 (31 mg, 96% purity) was used in the next synthetic step without further purification.

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
  7. customThe residue (31 mg, 96% purity) was used in the next synthetic step without further purification

출처 및 근거

ORD 기록
ord-34cbb4aae7944eec84afb770be7c1580
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

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