Trifluoroacetic acid → (1-methyl-cyclohexyl)-[2-(4-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677486

반응식

HRID 1677486 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[C:22]4[C:28]([C:29]([C:31]5([CH3:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[O:30])=[CH:27][NH:26][C:23]4=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:37][C:31]1([C:29]([C:28]2[C:22]3[C:23](=[N:24][CH:25]=[C:20]([C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:15][CH:16]=4)[N:21]=3)[NH:26][CH:27]=2)=[O:30])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 595406974-{4-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59540630(1-methyl-cyclohexyl)-[2-(4-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone수율 89.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-{4-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (35 mg, 0.069 mmol) in DCM (5 ml), at 0° C., was treated with TFA (0.15 ml, 2.01 mmol). The reaction mixture was stirred at room temperature for 16 hours, and then refluxed for 1.5 hours. The reaction mixture was concentrated to dryness, and the resulting residue was partitioned between sat. NaHCO3 and EtOAc. The organic layers were collected, dried over MgSO4, filtered, and concentrated providing 25 mg (89%) of (1-methyl-cyclohexyl)-[2-(4-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a yellow solid. MP 214-216° C., M+H=404.

후처리

  1. temperaturerefluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe resulting residue was partitioned between sat. NaHCO3 and EtOAc
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b2d2bcc3e66a475faac9e8023f573b8f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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