Hydrochloric Acid → HCID 178425386, compound

HRID 415107Notes

Reaction equation

HRID 415107 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:36])=[C:7]([NH:9][C:10]([C:12]2[N:13]=[CH:14][NH:15][C:16]=2[C:17]([NH:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[CH:28][C:22]=3[N:21]=2)=[O:18])=[O:11])[CH:8]=1.Cl>O1CCOCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:36])=[C:7]([NH:9][C:10]([C:12]2[N:13]=[CH:14][NH:15][C:16]=2[C:17]([NH:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[CH:28][C:22]=3[N:21]=2)=[O:18])=[O:11])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178425387HCID 178425387, compound

Product 1

HCID 178425386HCID 178425386, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N4-(5-Chloro-2-methylphenyl)-N5-[5-(piperidin-4-yloxy)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide hydrochloride was treated with 4M hydrogen chloride in 1,4-dioxane for 48 hours at room temperature to give N4-(5-chloro-2-methylphenyl)-N5-[5-(piperidin-4-yloxy)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide as its hydrochloride salt in 61% yield. 1H-NMR (400 MHz, DMSO-d6) δ 14.00 (br s, 1H), 11.95 (br s, 1H), 10.62 (br s, 1H), 9.23 (d, 2H), 8.30 (s, 1H), 7.78 (br s, 1H), 7.56 (d, 1H), 7.39 (dd, 1H), 7.30 (dd, 1H), 7.23 (s, 1H), 7.03 (dd, 1H), 4.76 (m, 1H), 3.23 (m, 2H), 3.04 (m, 2H), 2.33 (s, 3H), 2.12 (m, 2H), 1.90 (m, 2H). MS (EI): 494 (MH+).

Sources & evidence

ORD record
ord-ba02a803c2f344198ebe3ab2660db47f
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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