Formaldehyde → HCID 178425385, compound

HRID 415106Notes

Reaction equation

HRID 415106 reaction equation
[CH2:1]=O.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:36])=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH:20][C:21]2[NH:25][C:24]3[CH:26]=[C:27]([N:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[CH:28]=[CH:29][C:23]=3[N:22]=2)=[O:19])=[O:12])[CH:9]=1.[Na]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:36])=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH:20][C:21]2[NH:22][C:23]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:31][CH2:32][N:33]([CH3:1])[CH2:34][CH2:35]4)=[CH:26][C:24]=3[N:25]=2)=[O:19])=[O:12])[CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5360545SodiumHCID 59349515HCID 59349515, compound

Product 1

HCID 178425385HCID 178425385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottom flask was charged with paraformaldehyde (2.0 mmol) and N4-(5-chloro-2-methylphenyl)-N5-(6-(piperazin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide (0.2 mmol), anhydrous DMF (5 mL) and sodium triacetoxybrohydride (1.0 mmol). The reaction mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure and purified by preparative scale —HPLC (aqueous ammonium acetate/acetonitrile) to give N4-(5-chloro-2-methylphenyl)-N5-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, MeOH-d4): δ 8.15 (s, 1H), 7.92 (s, 1H), 7.38 (d, 3H), 7.24 (s, 1H), 7.18-7.14 (m, 2H), 6.96 (dd, 1H), 3.35-3.25 (m, 4H), 3.00-2.90 (m, 4H), 2.57 (s, 3H), 2.40 (s, 3H). MS (EI): 493 (MH+).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. custompurified by preparative scale —HPLC (aqueous ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-ec092414178549e1b1e0c69a54eff51f
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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