Potassium Carbonate → HCID 58487933, compound

HRID 1406384Notes

Reaction equation

HRID 1406384 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2([NH:13][C:14]([C:16]3[CH:17]=[N:18][CH:19]=[N:20][CH:21]=3)=[O:15])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.F[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[C:33]([F:36])([F:35])[F:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CC(C)=O>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([O:1][C:2]2[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]3([NH:13][C:14]([C:16]4[CH:21]=[N:20][CH:19]=[N:18][CH:17]=4)=[O:15])[CH2:12][CH2:11]3)=[O:9])=[CH:4][CH:3]=2)=[C:26]([C:33]([F:34])([F:35])[F:36])[CH:27]=1)#[N:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 67448187HCID 67448187, compound

Product 1

HCID 58487933HCID 58487933, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.32 mmol) of pyrimidin-5-carboxylic acid[1-(4-hydroxy-benzylcarbamoyl)-cyclopropyl]-amide, 60.5 mg (0.32 mmol) of 4-fluoro-3-trifluoromethyl-benzonitrile and 110 mg (0.8 mmol) of potassium carbonate in 5 mL DMF was stirred for two hours at 110° C. After cooling the mixture was diluted with approx. 3 mL acetone, filtered and evaporated down. The crude product thus obtained was purified by column chromatography (reversed phase).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationfiltered
  3. customevaporated down

Sources & evidence

ORD record
ord-e1daebc808ee4a6a91aa543355757b0e
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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