Acetaldehyde → HCID 59349428, compound

HRID 415069Notes

Reaction equation

HRID 415069 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][C:25]=1[CH3:37])=[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][C:25]=1[CH3:37])=[O:22])=[O:15]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 24983964HCID 24983964, compound

Product 1

HCID 59349428HCID 59349428, 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-(2-methyl-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.0465 g, 0.1 mmol) was added, followed by a DMF solution (3.0 ml) of sodium triacetoxyborohydride (0.106 g, 0.5 mmol). The reaction mixture was stir 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]-2-methylphenyl}-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): δ 9.49 (s, 1H), 8.22 (s, 1H), 7.52 (m, 1H), 7.41 (m, 2H), 7.23 (m, 2H), 6.97 (m, 2H), 4.75 (m, 1H), 3.54 (m, 2H), 3.37 (m, 3H), 3.12 (m, 4H), 2.24 (m, 4H), 1.22 (s, 3H); MS (EI): 488.7 (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-cb30d0752b964709b4c4c9c3e88f26a2
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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