Phenyl isocyanate → HCID 59349533, compound

HRID 415092Notes

Reaction equation

HRID 415092 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[NH:17][CH:16]=[N:15][C:14]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][C:22]=1[CH3:33])=[O:19])=[O:12].[C:34]1([N:40]=[C:41]=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[NH:17][CH:16]=[N:15][C:14]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:28][CH2:29][N:30]([C:41]([NH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:42])[CH2:31][CH2:32]2)=[CH:23][C:22]=1[CH3:33])=[O:19])=[O:12]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 59349445HCID 59349445, compound

Product 1

HCID 59349533HCID 59349533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N5-(1H-Benzo[d]imidazol-2-yl)-N4-(2-methyl-4-(piperazin-1-yl)phenyl)-1H-imidazole-4,5-dicarboxamide (1 equivalent) and dichloromethane were stirred for 5 minutes. Phenyl isocyanate (1.5 equiv) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was evaporated under reduced pressure. The resulting crude product was purified by reverse phase HPLC (aqueous ammonium acetate/acetonitrile to give N5-1H-benzimidazol-2-yl-N4-(2-methyl-4-{4-[(phenylamino)carbonyl]piperazin-1-yl}phenyl)-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): δ 8.86 (s, br, 1H), 8.38 (s, br, 1H), 7.67 (m, 2H), 7.52 (m, 3H), 7.43 (m, 3H), 7.26 (m, 2H), 6.97 (m, 1H), 3.84 (s, br, 4H), 3.41 (s, br, 4H), 2.33 (s, 3H). MS (EI): 564 (MH+).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customThe resulting crude product was purified by reverse phase HPLC (aqueous ammonium acetate/acetonitrile

Sources & evidence

ORD record
ord-7f6dd82582024799884dd916f3ab8134
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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