HCID 69070759, compound → HCID 69067477, compound

HRID 2111793Notes

Reaction equation

HRID 2111793 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]([NH:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[O:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:9][CH:10]=1)(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[C:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]([NH:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[O:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 69070759HCID 69070759, compound

Product 1

HCID 69067477HCID 69067477, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (0.47 g) in 2M HCl(aq) (5 mL) was heated at reflux until complete consumption of the starting material as judged by LC-MS (approximately 40 min). The crude reaction mixture was concentrated in vacuo and the residue dried in vacuo to afford 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide that was used without further purification. 1H-NMR (DMSO-d6, 400 MHz): δ 3.5-5.5 (br), 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 until complete consumption of the starting material
  2. customas judged by LC-MS (approximately 40 min)
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-44beebc310f141fe920daf8a0929ea63
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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