Acetic Anhydride → HCID 86759315, compound

HRID 1838268Notes

Reaction equation

HRID 1838268 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([N:18]2[CH2:23][C@@H:22]([CH3:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=3)[CH2:20][C@@H:19]2[CH3:37])=[O:17])[CH:12]=[CH:11][N:10]=1>N1C=CC=CC=1>[C:5]([NH:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([N:18]2[CH2:23][C@@H:22]([CH3:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=3)[CH2:20][C@@H:19]2[CH3:37])=[O:17])[CH:12]=[CH:11][N:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9844982HCID 9844982, compound

Product 1

HCID 86759315HCID 86759315, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 1.2 ml portion of acetic anhydride was added to 10 ml of pyridine solution containing 0.51 g of (+/−)-trans-N-(2-amino-pyrimidin-4-yl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide synthesized in the same manner as described in Example 21, and the mixture was stirred at room temperature for about 12 hours and then heated at 70° C. for about 1 hour. The reaction solution was evaporated under reduced pressure, and the thus obtained residue was mixed with 0.5 N aqueous sodium hydroxide and extracted with chloroform. The thus obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and then the crude product obtained by evaporating the solvent was separated by a silica gel column chromatography to obtain 0.46 g of the title compound from chloroform-methanol-28% aqueous ammonia (500:9:1, v/v/v) eluate. Thereafter, this was crystallized from ethyl acetate-hexane solution to obtain 0.31 g of white crystals.

Workup

  1. customsynthesized in the same manner
  2. temperatureheated at 70° C. for about 1 hour
  3. customThe reaction solution was evaporated under reduced pressure
  4. additionthe thus obtained residue was mixed with 0.5 N aqueous sodium hydroxide
  5. extractionextracted with chloroform
  6. washThe thus obtained organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe crude product obtained
  9. customby evaporating the solvent
  10. customwas separated by a silica gel column chromatography

Sources & evidence

ORD record
ord-25f7cac4a2ff4550a9da63ef65131b89
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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