Water → Cyclopentyl-{4-[4-(4-ethoxy-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone

HRID 1931750노트

반응식

HRID 1931750 반응식
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH2:16]([O:18][C:19]1[CH:40]=[CH:39][C:22]([O:23][C:24]2[N:29]=[CH:28][N:27]=[C:26]3[N:30]([CH:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[N:31]=[CH:32][C:25]=23)=[C:21]([F:41])[CH:20]=1)[CH3:17].C(N(C(C)C)CC)(C)C.O>ClCCl>[CH:1]1([C:6]([N:36]2[CH2:37][CH2:38][CH:33]([N:30]3[C:26]4=[N:27][CH:28]=[N:29][C:24]([O:23][C:22]5[CH:39]=[CH:40][C:19]([O:18][CH2:16][CH3:17])=[CH:20][C:21]=5[F:41])=[C:25]4[CH:32]=[N:31]3)[CH2:34][CH2:35]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 962WaterHCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 669153124-(4-ethoxy-2-fluoro-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2회

생성물 1

HCID 57964888Cyclopentyl-{4-[4-(4-ethoxy-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone수율 87.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Cyclopentanecarbonyl chloride (10 mg, 0.078 mmol) was added to a mixture of 4-(4-ethoxy-2-fluoro-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 29; 28 mg, 0.078 mmol), and diisopropylethylamine (30 mg, 0.235 mmol) in dichloromethane (2 mL). The reaction mixture was stirred at room temperature overnight. Water was added to quench the reaction and the aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried (sodium sulfate), filtered, evaporated and purified by flash chromatography on silica gel, eluting with 4% methanol/dichloromethane to give cyclopentyl-{4-[4-(4-ethoxy-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidin-1-yl}-methanone (31 mg, 87%) as a white solid. Mass spectrum MH+=454.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash chromatography on silica gel
  8. washeluting with 4% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-7c4920e6a29949649a86f2cd8161fab8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

반응 노트

불러오는 중…