1-Methylpiperazine → 1-[(1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-7-yl)carbonyl]-4-methylpiperazine

HRID 2068943Notes

Reaction equation

HRID 2068943 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.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]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][C:15]([C:21]([N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)=[O:23])=[CH:14][CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 591986821-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid

Product 1

HCID 591987421-[(1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-7-yl)carbonyl]-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

1-Cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid as synthesized in above Example 58, 218 mg, N-methylpiperazine 85 μL, 1-hydroxybenzotriazole monohydrate 161 mg, 4-dimethylaminopyridine 17 mg, pyridine 4.8 mL and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 202 mg were mixed and stirred overnight under nitrogen atmosphere. After distilling the solvent off, ethyl acetate, tetrahydrofuran and saturated aqueous sodium hydrogencarbonate solution were added, and the organic layer was separated. The organic layer was washed with water and dried over magnesium sulfate. After distilling the solvent off, 67 mg of the title compound was obtained upon recrystallization from diethyl ether.

Workup

  1. additionwere mixed
  2. distillationAfter distilling the solvent off, ethyl acetate, tetrahydrofuran and saturated aqueous sodium hydrogencarbonate solution
  3. additionwere added
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationAfter distilling the solvent off, 67 mg of the title compound
  8. customwas obtained upon recrystallization from diethyl ether

Sources & evidence

ORD record
ord-11038fbe25a442fa82300603dfbe4b71
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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