Potassium Carbonate → N-(2-(3-cyano-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-2,2,2-trifluoro-N-methylacetamide

HRID 64282Notes

Reaction equation

HRID 64282 reaction equation
[C:1]([C:3]1[C:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[N:5][N:6]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:10][CH2:9][NH:8][C:7]=12)#[N:2].[C:39]([O-])([O-])=O.[K+].[K+]>CC(C)=O.CI>[C:1]([C:3]1[C:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[N:5][N:6]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]([CH3:39])[C:19](=[O:24])[C:20]([F:21])([F:23])[F:22])[CH2:10][CH2:9][NH:8][C:7]=12)#[N:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 136928091HCID 136928091, compound

Product 1

HCID 136928075N-(2-(3-cyano-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-2,2,2-trifluoro-N-methylacetamideYield 100%

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of N-(2-(3-cyano-2-(4-(4-fluorophenoxyl)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-2,2,2-trifluoroacetamide (187 mg, 0.36 mmol) in acetone (10 mL) was added K2CO3 (100 mg, 0.72 mmol) and CH3I (15 drops). After stirring at RT for 2 hr, the mixture was filtered. The filtrate was concentrated to afford 192 mg (100%) of N-(2-(3-cyano-2-(4-(4-fluorophenoxyl)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-2,2,2-trifluoro-N-methylacetamide as yellow solid. MS (ESI) m/e [M+1]+ 535.8.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7e0bcd884c2f484692c6b4b3cfd896b6
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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