Acetaldehyde → HCID 59349512, compound

HRID 415058Notes

Reaction equation

HRID 415058 reaction equation
[CH:1](=O)[CH3:2].[NH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][C:14]([C:16]1[NH:20][CH:19]=[N:18][C:17]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1)=[O:22])=[O:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CN(C=O)C>[NH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][C:14]([C:16]1[NH:20][CH:19]=[N:18][C:17]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]2[CH2:36][CH2:35][N:34]([CH2:1][CH3:2])[CH2:33][CH2:32]2)=[CH:26][CH:25]=1)=[O:22])=[O:15]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 24985086HCID 24985086, compound

Product 1

HCID 59349512HCID 59349512, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetaldehyde (0.088 g, 2.0 mmol) was weighed out into a dry 25 ml round bottom flask. N5-(1H-benzo[d]imidazol-2-yl)-N4-(4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.0446 g, 0.1 mmol) was added, followed by DMF (3.0 ml) of sodium triacetoxyborohydride (0.106 g, 0.5 mmol). 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) to give N5-1H-benzimidazol-2-yl-N4-{4-[(1-ethylpiperidin-4-yl)oxy]phenyl}-1H-imidazole-4,5-dicarboxamide as an grey-white solid. 1H-NMR (DMSO-d6) 8.05 (s, 1H), 7.68 (d, 2H), 7.43 (s, br 2H), 7.05 (dd, 2H), 6.93 (d, 2H), 4.31 (m, 1H), 2.65 (m, 2H), 2.29 (q, 2H), 2.14 (m, 2H), 1.88 (m, 2H), 1.59 (m, 2H), 0.95 (t, 3H). MS (EI): 474 (MH+).

Workup

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

Sources & evidence

ORD record
ord-bf32e8fcc188421091b87850182c1f58
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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