Benzenesulfonyl chloride → HCID 59349423, compound

HRID 415091Notes

Reaction equation

HRID 415091 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([S:40](Cl)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCN(C(C)C)C(C)C>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]([S:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)(=[O:42])=[O:41])[CH2:31][CH2:32]2)=[CH:23][C:22]=1[CH3:33])=[O:19])=[O:12]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59349445HCID 59349445, compound

Product 1

HCID 59349423HCID 59349423, compoundYield 43%

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), dichloromethane, benzenesulfonyl chloride (1.5 equiv), and DIEA (1.5 equiv.) were added and stirred at room temperature. After 1 hour, LC-MS indicated the reaction was complete. 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-(phenylsulfonyl)piperazin-1-yl]phenyl}-1H-imidazole-4,5-dicarboxamide in 43% yield. 1H-NMR (400 MHz, DMSO-d6): δ 10.9 (s, br, 1H), 8.36 (s, 1H), 7.80 (m, 2H), 7.73-7.64 (m, 4), 7.43 (m, 2H), 7.33 (m, br, 1H), 6.97 (m, br, 2H), 3.31 (s, br, 4H), 3.09 (s, br, 4H). 2.24 (s, 3H). MS (EI): 585 (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-786ec042ab434e8c849e2d39647ee157
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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