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 2279114Notes

Reaction equation

HRID 2279114 reaction equation
[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]

Participants

7

Reactant 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

Product 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 esterYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6adc8d6870a346118c9b98d2dfcd1ab9
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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