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 1853959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853959
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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%]

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae25f12d18f049cfb98d9c4a01225678
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962637B2

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