Ammonium formate → HCID 11219535, compound

HRID 2054319Notes

Reaction equation

HRID 2054319 reaction equation
[CH:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[N:5]1[CH:15]1[CH2:20][CH2:19][N:18](CC2C=CC=CC=2)[CH2:17][CH2:16]1)([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[C].[Pd]>[CH:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[N:5]1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22939251HCID 22939251, compound

Product 1

HCID 11219535HCID 11219535, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Into a solution of 2.30 g (6.33 mmol) of 4-isopropyl-3-(1-benzylpiperidin-4-yl)-3,4-dihydro-2(1H)-quinazolinone in 127 ml of methanol, 0.23 g (0.11 mmol) of 10% palladium carbon (50% wet) and 1.60 g (25.3 mmol) of ammonium formate were added and refluxed under stirring and heating for 4 hours. After cooling to room temperature, the reaction mixture was filtered. To the filtrate, 0.5% aqueous sodium hydroxide solution and chloroform were added and stirred. The separated oil layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform/methanol/triethylamine 90/10/5) to give 1.73 g (6.33 mmol) of the above-titled compound.

Workup

  1. temperaturerefluxed
  2. temperatureheating for 4 hours
  3. filtrationthe reaction mixture was filtered
  4. additionTo the filtrate, 0.5% aqueous sodium hydroxide solution and chloroform were added
  5. stirringstirred
  6. dry with materialThe separated oil layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrated residue was purified by silica gel column chromatography (chloroform/methanol/triethylamine 90/10/5)

Sources & evidence

ORD record
ord-fd78dfee215447b4ba54d0210624c204
Source dataset
uspto-grants-2008_02
Patent number
US07329665B2

Reaction notes

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