Acetaldehyde → Methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoate

HRID 1628451Notes

Reaction equation

HRID 1628451 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:28](=O)[CH3:29].[C:31](O[BH3-])(=O)[CH3:32].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:9]1[N:8]([CH2:20][CH:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:28][CH3:29])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

7

Reactant 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68762018Methyl 4-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}-3-hydroxybutanoate

Product 1

HCID 68765145Methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoateYield 97.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of methyl 4-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}-3-hydroxybutanoate (Reference Example 82; 760 mg, 1.85 mmol) in methanol (19 mL) and acetic acid (0.380 mL) was added acetaldehyde (0.692 mL, 11.1 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (2.35 g, 11.1 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 15 hr, the mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give the title compound as a solid (838 mg, 1.80 mmol, 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-8700f31757f64e6f9833b2b2a99c253b
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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