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

HRID 1677486

反応式

HRID 1677486 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b2d2bcc3e66a475faac9e8023f573b8f
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

関連ノート

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