1,1'-Carbonyldiimidazole → HCID 58575010, compound

HRID 1807841Notes

Reaction equation

HRID 1807841 reaction equation
[NH2:1][C:2]1[C:3]([N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>ClC1C=CC=CC=1Cl>[CH:18]1([C:14]2[N:13]3[C:3]4[C:2]([NH:1][C:23](=[O:24])[C:17]3=[CH:16][N:15]=2)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:12])[CH:4]=4)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58575267HCID 58575267, compound

Product 1

HCID 58575010HCID 58575010, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 1.79 g of methyl 5-amino-4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methylbenzoate, 1.04 g of 1,1′-carbonyldiimidazole, and 18 mL of 1,2-dichlorobenzene was stirred at 190° C. for 3 hours. After air-cooling, the reaction mixture was purified by silica gel column chromatography (chloroform/methanol) to obtain 0.91 g of methyl 1-cyclopentyl-8-methyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylate.

Workup

  1. temperatureAfter air-cooling
  2. customthe reaction mixture was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e330d867cd434258ad26fc180ccba2f2
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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