Dimethylacetamide → 1-Cyclohexyl-7-(3-methyl-[1,2,4]-oxadiazol-5-yl)imidazo-[1,5-a]quinoxalin-4(5H)-one

HRID 72740Notes

Reaction equation

HRID 72740 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][C:15]([C:21]([OH:23])=O)=[CH:14][CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C(=O)C.C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:43][C:44](=[NH:46])[CH3:45]>O>[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][C:15]([C:21]2[O:23][N:46]=[C:44]([CH3:45])[N:43]=2)=[CH:14][CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 682631,1'-CarbonyldiimidazoleHCID 591986821-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 591987781-Cyclohexyl-7-(3-methyl-[1,2,4]-oxadiazol-5-yl)imidazo-[1,5-a]quinoxalin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxyic acid as synthesized in Example 58, 300 mg, N,N-dimethylacetamide 5 mL and 1,1′-carbonyldiimidazole 266 mg were mixed and stirred for 30 minutes at room temperature. To the reaction liquid 143 mg of N-hydroxyacetamidine was added, followed by 12 hours' stirring at 110° C. After returning it to the room temperature, water was added thereto and the precipitated matter was recovered by filtration. Drying the precipitate by heating under reduced pressure, 210 mg of the title compound was obtained.

Workup

  1. additionwere mixed
  2. additionwas added
  3. waitfollowed by 12 hours
  4. stirring' stirring at 110° C
  5. additionwas added
  6. filtrationthe precipitated matter was recovered by filtration
  7. customDrying the precipitate
  8. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-1c46a9181e0e458d8922519b02448324
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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