Trifluoroacetic acid → benzyl 4-[4-amino-3-(4-amino-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate

HRID 897806

反応式

HRID 897806 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[CH2:29][CH2:28]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(OC(C)(C)C)=O)=[C:13]([O:25][CH3:26])[CH:12]=3)[C:3]=12.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:34])[CH2:29][CH2:28]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:25][CH3:26])[CH:12]=3)[C:3]=12

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 22346687benzyl 4-(4-amino-3-{4-[(tert-butoxycarbonyl)amino]-3-methoxyphenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate

生成物 1

HCID 22346984benzyl 4-[4-amino-3-(4-amino-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate収率 94.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of benzyl 4-(4-amino-3-{4-[(tert-butoxycarbonyl)amino]-3-methoxyphenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (7.68 g, 0.0134 mol) in dichloromethane (10 mL) was added a 25% solution of trifluoroacetic acid in dichloromethane at 0° C. The mixture was stirred under an atmosphere of nitrogen at room temperature for 18 hours. The solvents were removed under reduced pressure. The residue was cooled to 0° C. and basified with an aqueous 5 N solution of sodium hydroxide. The aqueous layer was extracted with dichloromethane (3×150 mL). The combined organic layer was washed with water and brine, and dried over magnesium sulfate. The solvents were removed under reduced pressure to give benzyl 4-[4-amino-3-(4-amino-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (6.02 g, 0.0127 mol).

後処理

  1. customThe solvents were removed under reduced pressure
  2. temperatureThe residue was cooled to 0° C.
  3. extractionThe aqueous layer was extracted with dichloromethane (3×150 mL)
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-cd58aa5032cb405880f5053c748a31b0
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

関連ノート

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