Hydrochloric Acid → HCID 178479721, compound

HRID 415081Notes

Reaction equation

HRID 415081 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[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH:20][C:21]1[CH:40]=[CH:39][C:24]([O:25][CH:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]2)=[C:23]([Cl:41])[CH:22]=1)=[O:19])=[O:12].[ClH:42]>O1CCOCC1>[ClH:41].[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[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH:20][C:21]1[CH:40]=[CH:39][C:24]([O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][C:22]=1[Cl:42])=[O:19])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452144HCID 178452144, compound

Product 1

HCID 178479721HCID 178479721, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A flask was charged with tert-butyl 4-(4-(4-(1H-benzo[d]imidazol-2-ylcarbamoyl)-1H-imidazole-5-carboxamido)-2-chlorophenoxy)piperidine-1-carboxylate (260 mg, 0.45 mmol), 4 N hydrogen chloride in 1,4-dioxane (1 mL, 4 mmol) and 1,4-dioxane (50 mL), and the reaction mixture was stirred for 15 hours at room temperature. The resulting solid was filtered off and air dried to give 0.228 g of N4-(1H-benzo[d]imidazol-2-yl)-N5-(2-chloro-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide hydrochloride (99% yield). 1H-NMR (400 MHz, DMSO-d6): δ 13.9 (s, br, 1H), 13.7 (s, 1H), 12.2 (s, 1H), 10.4 (s, 1H), 8.41-8.39 (m, 1H), 8.15 (s, 1H), 8.01 (s, 1H), 7.45 (s, 2H), 7.07 (s, 2H). MS (EI): 450 (MH+).

Workup

  1. filtrationThe resulting solid was filtered off
  2. customair dried

Sources & evidence

ORD record
ord-f2d5163d918e481685a23dcbd5f78b93
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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