2-Aminopyridine → 1-Cyclohexyl-4-oxo-N-(2-pyridyl)-4,5-dihydroimidazo[1,5-a]-quinoxaline-8-carboxamide

HRID 72734Notes

Reaction equation

HRID 72734 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][CH:15]=[C:14]([C:21](O)=[O:22])[CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[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][CH:15]=[C:14]([C:21]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[O:22])[CH:13]=4)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59198793HCID 59198793, compound

Product 1

HCID 591988861-Cyclohexyl-4-oxo-N-(2-pyridyl)-4,5-dihydroimidazo[1,5-a]-quinoxaline-8-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-8-carboxyic acid as synthesized in above Example 103, 405 mg, 2-aminopyridine 184 mg, 1-hydroxybenzotriazole monohydrate 299 mg, 4-dimethylaminopyridine 31 mg, pyridine 8.5 mL and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 375 mg were mixed and stirred for 23 hours. After distilling the solvent off, ethyl acetate and saturated aqueous sodium hydrogencarbonate solution were added to the residue and stirred. The crystals were recovered by filtration and washed successively with water and ethyl acetate. The crystals were heat-suspended in 20 mL of acetone, recovered by filtration and washed with acetone. Drying the crystals, 213 mg of the title compound was obtained.

Workup

  1. additionwere mixed
  2. distillationAfter distilling the solvent off, ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. additionwere added to the residue
  4. stirringstirred
  5. filtrationThe crystals were recovered by filtration
  6. washwashed successively with water and ethyl acetate
  7. filtrationrecovered by filtration
  8. washwashed with acetone
  9. customDrying the crystals

Sources & evidence

ORD record
ord-73484e36ca6c4eb3b7ba46f0b4b9d2e1
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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