Ammonium formate → HCID 54761632, compound

HRID 589868Notes

Reaction equation

HRID 589868 reaction equation
[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14](Cl)=[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]([C:17]([NH2:19])=[O:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]([C:17]([NH2:19])=[O:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54761997HCID 54761997, compound

Product 1

HCID 54761632HCID 54761632, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.866 g (2.31 mmol) of N2-tert-butyl-6-chloro-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide, 6.0 g (95 mmol) of ammonium formate and 0.20 g (0.09 mmol) of 10% palladium-on-charcoal containing 50% water in 50 ml of methanol is refluxed for 6 hours. After cooling, the mixture is filtered through Celite and the Celite is rinsed with dichloromethane. The filtrate is then concentrated under reduced pressure and the residue is taken up in dichloromethane. The solution is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The product is then purified by chromatography on a column of 40 g of silica gel, eluting with a mixture of 95 to 50% ethyl acetate in dichloromethane, to give 0.31 g of N2-tert-butyl-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a white solid after crystallizing from diethyl ether and drying.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered through Celite
  4. washthe Celite is rinsed with dichloromethane
  5. concentrationThe filtrate is then concentrated under reduced pressure
  6. washThe solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe product is then purified by chromatography on a column of 40 g of silica gel
  10. washeluting with a mixture of 95 to 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-92179d5d99d94121a145ea7ce19d372c
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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