Hydrochloric Acid → HCID 69067476, compound

HRID 2111811Notes

Reaction equation

HRID 2111811 reaction equation
[ClH:1].C([NH:5][C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[O:22])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1)(=O)C>>[ClH:1].[ClH:1].[NH2:5][C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[O:22])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69070759HCID 69070759, compound

Product 1

HCID 69067476HCID 69067476, compound

Procedure

An aqueous HCl (2M, 5 mL) solution of 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (0.47 g) was heated at reflux. After 40 min, the crude reaction mixture was evaporated under reduced pressure at rt and dried in vacuo to afford 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide dihydrochloride as a purple solid. 1H-NMR (DMSO-d6, 400 MHz): δ 4.00 (brs, 2H), 4.72 (d, J=5.2 Hz, 2H), 7.24 (d, J=7.6 Hz, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.44 (s, 1H), 7.56 (t, J=8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 8.10-8.50 (m, 2H), 8.47 (s, 1H), 8.59 (d, J=8.0 Hz, 1H), 8.85 (1H, J=5.6 Hz, 1H), 8.96 (s, 1H), 9.25 (s, 1H), 9.64 (t, J=5.6 Hz, 1H). MS (ES+): m/z 344 [MH+].

Workup

  1. temperatureat reflux
  2. customthe crude reaction mixture
  3. customwas evaporated under reduced pressure at rt
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e6020ef7eb904a32bea5eb1fa6cdd22b
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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