Hydrochloric Acid → 2-(6-(piperazin-1-yl)pyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide hydrochloride

HRID 85100Notes

Reaction equation

HRID 85100 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[C:17]2[N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[N:22][CH:23]=3)[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8].[ClH:37]>>[ClH:37].[N:24]1([C:21]2[N:22]=[CH:23][C:18]([C:15]3[NH:14][C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([C:7]([NH:6][C:2]5[S:1][CH:5]=[CH:4][N:3]=5)=[O:8])[C:17]=4[N:16]=3)=[CH:19][CH:20]=2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86653786tert-butyl 4-(5-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 866537872-(6-(piperazin-1-yl)pyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide hydrochloride

Procedure

A mixture containing tert-butyl 4-(5-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperazine-1-carboxylate (8; 20 mg, 0.039 mmol) in methanolic HCl (3N, 2 mL) was stirred at room temperature for 18 h. The precipitated solids were collected by filtration, washed with MeOH and dried to afford 2-(6-(piperazin-1-yl)pyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide hydrochloride (Compound 251) as a pale yellow solid (21 mg). MS (ESI) calcd for C20H19N7OS (m/z): 405.14; found: 406 [M+H].

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. washwashed with MeOH
  3. customdried

Sources & evidence

ORD record
ord-d4e4bc3c29564546ac55315a51ab6b6f
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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