Acetic Acid → HCID 178438190, compound

HRID 634462Notes

Reaction equation

HRID 634462 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:37])[C:24]4[C:29]([C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:12]=[N:13][C:14]([O:17]C)=[N:15][CH:16]=3)[C:3]=12.CC(O)=O>Br.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:37])[C:24]4[C:29]([C:30]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:12]=[N:13][C:14]([OH:17])=[N:15][CH:16]=3)[C:3]=12

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 118131216HCID 118131216, compound

Product 1

HCID 178438190HCID 178438190, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

3-(1-(4-amino-3-(2-methoxypyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one (Example 55, 23.3 mg, 0.047 mmol) was dissolved in HBr 33% in CH3COOH (1 ml, 0.047 mmol) and stirred at rt for 1 h. The reaction was then diluted with water (3 mL) and the resulting mixture purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile to give the title compound (20 mg, 88%) as a white solid.

Workup

  1. customthe resulting mixture purified via reverse phase chromatography

Sources & evidence

ORD record
ord-9dda9bd2c13348b7a7bf7a7498c0a0c0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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