Sodium Acetate → 3-[2-(4-Chloro-phenylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-4-methyl-N-(3-trifluoromethylphenyl)benzamide

HRID 2092594Notes

Reaction equation

HRID 2092594 reaction equation
CN(C)[CH:3]1[C:8](=O)[CH2:7][CH2:6][N:5]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[O:14])[C:4]1=C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([NH2:42])=[NH:41])=[CH:35][CH:34]=1.[C:43]([O-])(=O)C.[Na+]>C(O)C.O>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:40]2[N:42]=[CH:43][C:3]3[CH2:4][N:5]([C:10]4[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=4[CH3:29])[C:13]([NH:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[CH:17]=4)=[O:14])[CH2:6][CH2:7][C:8]=3[N:41]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 866756433-(3-Dimethylamino-methylene-4-oxo-piperidin-1-yl)-4-methyl-N-(3-trifluoromethyl-phenyl)benzamideHCID 178512500HCID 178512500, compound

Product 1

HCID 673295863-[2-(4-Chloro-phenylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-4-methyl-N-(3-trifluoromethylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3-Dimethylamino-methylene-4-oxo-piperidin-1-yl)-4-methyl-N-(3-trifluoromethyl-phenyl)benzamide (17.9 gm, 41.7 mmol) in Ethanol (250 ml) were added N-(4-Chloro-phenyl)-guanidine (28.32 gm, 167 mmol) and sodium acetate (27.32 gm, 334 mmol) and solution was heated under reflux for 12 hours. After cooling to room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine and dried [sodium sulfate] and evaporated. The crude product obtained was purified by silica gel chromatography using 5-10% methanol/chloroform as eluent to give pure desired product i.e., 3-[2-(4-Chloro-phenylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-4-methyl-N-(3-trifluoromethyl phenyl)benzamide [28] as off white solid. [yield: 1.83 gm, 8.2%]

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried [sodium sulfate]
  6. customevaporated
  7. customThe crude product obtained
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-e3bbfa27b33a4f70a3e38668323b6ed4
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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