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

HRID 1677480ノート

反応式

HRID 1677480 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e45c4423a39c4070ace18956e3601aec
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

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