Triethylamine → N-(2,6-dimethylphenyl)hexahydro-3,3-dimethyl-2-(1-methylethyl)-1-oxoimidazo[1,5-a]pyrazine-7(8H)-acetamide

HRID 35332

Reaction equation

HRID 35332 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[CH3:14][C:15]1([CH3:28])[N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH:18]2[C:17](=[O:24])[N:16]1[CH:25]([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C)C=O>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:22]1[CH2:21][CH2:20][N:19]2[C:15]([CH3:14])([CH3:28])[N:16]([CH:25]([CH3:26])[CH3:27])[C:17](=[O:24])[CH:18]2[CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideHCID 21295654hexahydro-3,3-dimethyl-2-(1-methylethyl)imidazo[1,5-a]pyrazin-1(5H)-one

Product 1

HCID 14230242N-(2,6-dimethylphenyl)hexahydro-3,3-dimethyl-2-(1-methylethyl)-1-oxoimidazo[1,5-a]pyrazine-7(8H)-acetamideYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 8.2 parts of 2-chloro-N-(2,6-dimethylphenyl)acetamide, 7.2 parts of hexahydro-3,3-dimethyl-2-(1-methylethyl)imidazo[1,5-a]pyrazin-1(5H)-one, 7 parts of N,N-diethylethanamine and 54 parts of N,N-dimethylformamide was stirred and heated for 3 hours at 75° C. After cooling to 0° C., the precipitate was filtered off and the filtrate was evaporated. The residue was dissolved in 300 parts of trichloromethane. This solution was washed with 50 parts of water, dried, filtered and evaporated. The residue was triturated in 2,2'-oxybispropane. After cooling to 0° C., the product was filtered off and dried, yielding 9.2 parts (72.7%) of N-(2,6-dimethylphenyl)hexahydro-3,3-dimethyl-2-(1-methylethyl)-1-oxoimidazo[1,5-a]pyrazine-7(8H)-acetamide; mp. 155° C. (intermediate 101).

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationthe precipitate was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in 300 parts of trichloromethane
  5. washThis solution was washed with 50 parts of water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was triturated in 2,2'-oxybispropane
  10. temperatureAfter cooling to 0° C.
  11. filtrationthe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-aefb654b87b7431f99ffecb3fefb8341
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Linked notes

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