Hydrochloric Acid → HCID 178423584, compound

HRID 415087Notes

Reaction equation

HRID 415087 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[C:6]([NH:8][C:9]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]([NH:18][C:19]2[NH:23][C:22]3[CH:24]=[CH:25][C:26]([N:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[CH:27][C:21]=3[N:20]=2)=[O:17])=[O:10])[CH:7]=1.[ClH:42]>CO.O1CCOCC1>[ClH:42].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:41])=[C:6]([NH:8][C:9]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]([NH:18][C:19]2[NH:23][C:22]3[CH:24]=[CH:25][C:26]([N:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)=[CH:27][C:21]=3[N:20]=2)=[O:17])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178423586HCID 178423586, compound

Product 1

HCID 178423584HCID 178423584, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-(2-{[(4-{[(5-bromo-2-methylphenyl)amino]carbonyl}-1H-imidazol-5-yl)carbonyl]amino}-1H-benzimidazol-5-yl)piperazine-1-carboxylate (2.5 g, 4 mmol) in methanol (100 mL) was added 4 N hydrogen chloride in 1,4-dioxane (20 mL). The solution was stirred at room temperature for 48 hours. The resulting suspension was filtered to give 2.0 g of N4-(5-bromo-2-methylphenyl)-N5-(5-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-imidazole-4,5-dicarboxamide hydrochloride. 1H-NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 1H), 12.50 (br s, 1H), 11.20 (br s, 1H), 9.28 (d, 1H), 9.00 (d, 1H), 8.39 (s, 1H), 7.86 (s, 1H), 7.60 (d, 1H), 7.42 (d, 1H), 7.31 (d, 1H), 7.21 (s, 1H), 7.03 (d, 1H), 4.23 (br s 2H), 3.94 (m, 2H), 3.33 (m, 2H), 2.91 (m, 2H), 2.29 (s, 3H), 2.11 (m, 1H), 1.94 (m, 2H), 1.54 (m, 2H). MS (EI): 553 (MH+).

Workup

  1. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-e41a3a17fa3a4f9496343859bccac630
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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