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 2279114노트

반응식

HRID 2279114 반응식
[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]

참가 물질

7

반응물 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

생성물 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 ester수율 100%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6adc8d6870a346118c9b98d2dfcd1ab9
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

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