Hydrochloric Acid → 4'-(2-(4-Cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylic acid

HRID 386636Notes

Reaction equation

HRID 386636 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH3:19])=[C:12]([O:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([O:36]C)=[O:35])=[CH:30][CH:29]=4)=[CH:23][C:22]=3[CH3:38])[N:11]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].CO.Cl>C1COCC1.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH3:19])=[C:12]([O:20][C:21]3[C:22]([CH3:38])=[CH:23][C:24]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([OH:36])=[O:35])=[CH:32][CH:33]=4)=[CH:25][C:26]=3[CH3:27])[N:11]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 57747379Methyl 4'-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylate

Product 1

HCID 577473884'-(2-(4-Cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4′-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3′,5′-dimethylbiphenyl-4-carboxylate (110 mg, 0.22 mmol) and lithium hydroxide (100 mg, 2.38 mmol) in) in a mixture of THF (3 mL), MeOH (1 mL), and H2O (1 mL) was stirred at rt for 3 h. The reaction mixture was diluted with H2O (5 mL) and acidified (1 N HCl). The resulting precipitate was collected by filtration to yield the desired compound (90 mg). MS (ESI): m/z 491 (M+1)+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-83b4e66db98b46c295ae51d705b121d8
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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