Pentanal → HCID 178476262, compound

HRID 415108Notes

Reaction equation

HRID 415108 reaction equation
[CH:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:40])=[C:12]([NH:14][C:15]([C:17]2[N:18]=[CH:19][NH:20][C:21]=2[C:22]([NH:24][C:25]2[NH:29][C:28]3[CH:30]=[C:31]([N:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)[CH:32]=[CH:33][C:27]=3[N:26]=2)=[O:23])=[O:16])[CH:13]=1.[Na]>CN(C=O)C>[C:1]([OH:6])(=[O:16])[CH3:2].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:40])=[C:12]([NH:14][C:15]([C:17]2[N:18]=[CH:19][NH:20][C:21]=2[C:22]([NH:24][C:25]2[NH:26][C:27]3[CH:33]=[CH:32][C:31]([N:34]4[CH2:35][CH2:36][N:37]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:38][CH2:39]4)=[CH:30][C:28]=3[N:29]=2)=[O:23])=[O:16])[CH:13]=1

Participants

5

Reactant 3

HCID 8063PentanalHCID 5360545SodiumHCID 59349461HCID 59349461, compound

Product 1

HCID 178476262HCID 178476262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottom flask was charged with pentanal (0.177 g, 2.0 mmol) and N4-(5-bromo-2-methylphenyl)-N5-(6-(piperazin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide (0.104 g 0.2 mmol), anhydrous DMF (5 mL) and sodium triacetoxybrohydride (0.212 g, 1.0 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and subsequently purified by preparative reverse phase HPLC (ammonium acetate/acetonitrile) to give N4-(5-bromo-2-methylphenyl)-N5-[5-(4-pentylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide acetate. 1H-NMR (400 MHz, DMSO-d6): δ 8.09 (s, 1H), 7.99 (d, 1H), 7.39 (dd, 1H), 7.29-7.3 (m, 2H), 6.87 (dd, 1H), 3.07 (t, 4H), 2.31 (t, 7H), 1.91 (s, 2H), 1.43-1.50 (m, 2H), 1.23-1.34 (m, 4H), 0.90 (t, 3H), MS (EI): 594.8 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customsubsequently purified by preparative reverse phase HPLC (ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-78cbc35e8358424abc33c0841496f63b
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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