Acetonitrile → (R)-1-[3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethanone

HRID 1471822Notes

Reaction equation

HRID 1471822 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([C@@H:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].CCN(C(C)C)C(C)C.C(#N)C>C1COCC1.O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:32])[CH3:31])[CH2:25]3)[N:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)[C:22]=12

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 582232723-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

Product 1

HCID 58223321(R)-1-[3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (6) (0.05 g) in THF (1 mL) was added acetic anhydride (12.8 μL) and DIPEA (23.1 μL). The reaction was stirred at room temperature for 2 hours. A sample of the reaction mixture was prepared for LC/MS analysis. 10 μL of the reaction mixture was diluted with H2O:ACN=6:4 to result in a 0.1 mg/mL preparation. LC/MS confirmed that the resulting product (having a m/z of 429) is the title compound.

Workup

  1. customA sample of the reaction mixture was prepared for LC/MS analysis

Sources & evidence

ORD record
ord-81e26634a056464a80756930f506bb0a
Source dataset
uspto-grants-2015_04
Patent number
US09012463B2

Reaction notes

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