Acetaldehyde → HCID 68773304, compound

HRID 1398833Notes

Reaction equation

HRID 1398833 reaction equation
C[CH:2]([OH:26])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[C:12]([NH2:16])=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25].[CH:27](=O)[CH3:28].[C:30](O[BH3-])(=O)[CH3:31].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:8]1[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:26])[C:11]2[C:12]([N:16]([CH2:27][CH3:28])[CH2:30][CH3:31])=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

7

Reactant 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68766832HCID 68766832, compound

Product 1

HCID 68773304HCID 68773304, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of methyl 5-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}pentan-1-ol (Reference Example 112; 308 mg, 1.85 mmol) in methanol (8 mL) and acetic acid (0.160 mL) was added acetaldehyde (0.304 mL, 4.88 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (1.03 g, 4.86 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 14 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 (317 mg, 0.729 mmol, 90%).

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-df9c2f32c4af4eb494aa9413e6fcb403
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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