Acetaldehyde → HCID 68762907, compound

HRID 1628455Notes

Reaction equation

HRID 1628455 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[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:25](=O)[CH3:26].[C:28](O[BH3-])(=O)[CH3:29].[Na+]>CO.C(O)(=O)C.C(OCC)(=O)C>[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:24])[CH2:22][OH:23])[C:7]2[C:2]([N:1]([CH2:25][CH3:26])[CH2:28][CH3:29])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

7

Reactant 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68762708HCID 68762708, compound

Product 1

HCID 68762907HCID 68762907, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}propane-1,2-diol (Reference Example 87; 630 mg, 1.72 mmol) in methanol (17 mL) and acetic acid (0.34 mL) was added acetaldehyde (0.642 mL, 10.3 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (2.18 g, 10.3 mmol) at 0° C. After 1 hr, the mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (714 mg, 1.69 mmol, 98%) as a colorless solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60fc0a5028b9448ab461b09d0a40e8c9
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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