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

HRID 1677480노트

반응식

HRID 1677480 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([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: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:16]4[CH:17]=[CH:18][CH:19]=[C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:15]=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 595406484-{3-[7-(1-Methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59540704(1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone수율 61.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (134 mg, 0.266 mmol) in DCM (10 ml) was treated with TFA (1.0 ml, 13.4 mmol) and allowed to stir for 16 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 giving a yellow solid. The yellow solid was filtered through a Buchner funnel and washed with 1:2 Et2O/Hex to provide 66 mg (61%) of (1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a pale yellow solid. M+H=404.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe resulting residue was partitioned between sat. NaHCO3 and EtOAc
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving a yellow solid
  8. filtrationThe yellow solid was filtered through a Buchner funnel
  9. washwashed with 1:2 Et2O/Hex

출처 및 근거

ORD 기록
ord-e45c4423a39c4070ace18956e3601aec
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

반응 노트

불러오는 중…