Hydrochloric Acid → HCID 178423585, compound

HRID 415088Notes

Reaction equation

HRID 415088 reaction equation
C=O.Cl.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:37])=[C:9]([NH:11][C:12]([C:14]2[N:15]=[CH:16][NH:17][C:18]=2[C:19]([NH:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:30][C:24]=3[N:23]=2)=[O:20])=[O:13])[CH:10]=1.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CN(C=O)C>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:37])=[C:9]([NH:11][C:12]([C:14]2[N:15]=[CH:16][NH:17][C:18]=2[C:19]([NH:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([N:31]4[CH2:32][CH2:33][N:34]([CH3:38])[CH2:35][CH2:36]4)=[CH:30][C:24]=3[N:23]=2)=[O:20])=[O:13])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178423584HCID 178423584, compound

Product 1

HCID 178423585HCID 178423585, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Paraformaldehyde (0.088 g, 2.0 mmol) was weighed out into a dry 25 ml round bottom flask. N4-(5-bromo-2-methylphenyl)-N5-(5-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-imidazole-4,5-dicarboxamide hydrochloride (0.0465 g, 0.1 mmol) was added, followed by sodium triacetoxyborohydride (0.106 g, 0.5 mmol) dissolved in DMF (3.0 ml). The reaction mixture was stirred at room temperature over night (16 hours). The reaction mixture was then treated with 1 mL of 1N hydrochloric acid and concentrated under reduced pressure. The resulting crude material was purified by reverse phase HPLC (ammonium acetate/acetonitrile) which gave N4-(5-bromo-2-methylphenyl)-N5-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): δ 9.83 (s, 1H), 8.28 (s, 1H), 7.88 (s, 1H), 7.45 (dd, 1H), 7.30 (m, 2H), 7.12 (m, 1H), 7.05 (m, 1H), 3.77 (d, 2H), 3.56 (d, 2H), 3.21 (d, 2H), 2.97 (m, 2H), 2.89 (s, 3H), 2.30 (s, 3H); MS (EI): 538.7 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting crude material was purified by reverse phase HPLC (ammonium acetate/acetonitrile) which

Sources & evidence

ORD record
ord-a39c5053e0b54a1798b779fe0e37ce47
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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