Acetone → 7-cyclopentyl-2-(5-(8-isopropyl-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

HRID 1850558노트

반응식

HRID 1850558 반응식
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]3[N:19]=[CH:20][C:21]4[CH:26]=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[N:24]([CH:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)[C:22]=4[N:23]=3)=[N:15][CH:16]=1)=[O:10])[CH2:2]2.[CH3:37][C:38]([CH3:40])=O>C(Cl)Cl>[CH:32]1([N:24]2[C:22]3[N:23]=[C:18]([NH:17][C:14]4[CH:13]=[CH:12][C:11]([C:9]([N:3]5[CH2:4][CH:5]6[N:8]([CH:38]([CH3:40])[CH3:37])[CH:1]([CH2:7][CH2:6]6)[CH2:2]5)=[O:10])=[CH:16][N:15]=4)[N:19]=[CH:20][C:21]=3[CH:26]=[C:25]2[C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[CH2:33][CH2:34][CH2:35][CH2:36]1

참가 물질

4

반응물 2

HCID 180AcetoneHCID 533786742-(5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

생성물 1

HCID 673564107-cyclopentyl-2-(5-(8-isopropyl-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (42 mg, 0.086 mmol) in 6 ml of DCM, acetone (0.6 ml) was added and the resulting reaction mixture was stirred for 1H at room temperature. Na(AcO)3BH (55 mg, 0.26 mmol) was added and the resulting reaction mixture was stirred at room temperature overnight. When LCMS showed the reaction was complete the reaction mixture was diluted with DCM, washed with sat NaHCO3 (2×), brine. The combined aqueous layers were backextracted with DCM and the combined organic layers were dried over Na2SO4, filtered and purified by column chromatography (0-20% MeOH/CHCl2) which gave 7-cyclopentyl-2-(5-(8-isopropyl-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (64 mg, 88% yield).

후처리

  1. customthe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. stirringwas stirred at room temperature overnight
  4. washwashed
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. custompurified by column chromatography (0-20% MeOH/CHCl2) which

출처 및 근거

ORD 기록
ord-f160e2fba7c346e2bcfa1f0d7973e37f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957074B2

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