Ammonium Chloride → 4-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279114ノート

反応式

HRID 2279114 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C:9]1([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[C:32]([CH:46]=O)[C:33]3[C:38]([CH3:39])=[N:37][N:36]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[C:34]=3[N:35]=2)=[C:26]([F:48])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClCCl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:46][C:32]2[CH:31]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:25][C:26]=3[F:48])[N:35]=[C:34]3[N:36]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[N:37]=[C:38]([CH3:39])[C:33]=23)[CH2:10][C:9]1([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 299224001,1-Dimethylethyl 2,2-dimethyl-1-piperazinecarboxylateHCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

生成物 1

HCID 900140094-[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester収率 100%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 106 mg 2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester in 5 ml of dichloromethane was added 200 mg of freshly prepared 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde. 143 mg of sodium triacetoxyborohydride and 15 mg of acetic acid were added and the reaction was stirred at r.t. for 16 h. The reaction was then diluted with dichloromethane and shaken with sat. aqueous ammonium chloride solution. The layers were separated and the organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. 318 mg (100%) of the crude title compound were obtained which were used in the next step without further purification.

後処理

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6adc8d6870a346118c9b98d2dfcd1ab9
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

読み込み中…