Ammonium formate → HCID 57867990, compound

HRID 425994Notes

Reaction equation

HRID 425994 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:20]=2[C:21]([NH:23][C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][C:30](=[O:35])[N:31]3[CH3:34])=[CH:26][CH:25]=2)=[O:22])[CH2:14][CH2:13]1)C1C=CC=CC=1>[C].[Pd].CO>[CH3:34][N:31]1[C:32]2[C:27](=[CH:26][CH:25]=[C:24]([NH:23][C:21](=[O:22])[C:20]3[CH:36]=[CH:37][C:38]([C:40]([F:42])([F:43])[F:41])=[CH:39][C:19]=3[NH:18][CH:15]3[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]3)[CH:33]=2)[CH2:28][CH2:29][C:30]1=[O:35]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 667038282-[(1-benzylpiperidin-4-yl)amino]-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide

Product 1

HCID 57867990HCID 57867990, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Palladium-carbon and ammonium formate were added to a methanol solution of 2-[(1-benzylpiperidin-4-yl)amino]-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide, followed by heating under reflux for 2 hours. After spontaneous cooling, Celite filtration was carried out and then the filtrate was concentrated under a reduced pressure. By purifying the residue by silica gel column chromatography, N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-(piperidin-4-ylamino)-4-(trifluoromethyl)benzamide was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. filtrationAfter spontaneous cooling, Celite filtration
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. customBy purifying the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-a48f162131e74623add66c301965ef07
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

Loading…