Acetic Acid → HCID 68764844, compound

HRID 1398900Notes

Reaction equation

HRID 1398900 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH2:21][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]=[C:4]([F:24])[CH:3]=1.[C:25](O)(=O)[CH3:26].[CH:29](=O)[CH3:30].C(O[BH3-])(=O)C.[Na+]>CO>[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][CH2:21][CH2:22][OH:23])[C:7]2[C:2]([N:1]([CH2:25][CH3:26])[CH2:29][CH3:30])=[CH:3][C:4]([F:24])=[CH:5][C:6]=2[N:10]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 177Acetaldehyde2×HCID 23670382Sodiumacetoxyborohydride2×HCID 68777299HCID 68777299, compound

Product 1

HCID 68764844HCID 68764844, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-{7-amino-2-[(2,4-dichlorophenyl)amino]-5-fluoro-1H-benzimidazol-1-yl}propan-1-ol (369 mg, 1.00 mmol) and acetic acid (0.5 mL) in methanol (10 mL) was added acetoaldehyde (374 μL, 6.00 mmol) at room temperature. After 30 min, sodium acetoxyborohydride (1.27 g, 6.00 mmol) was added. After 4 h, the mixture was cooled down to 0° C. Then acetic acid (0.5 mL) and acetoaldehyde (374 μL, 6.00 mmol) was added. After 30 min, sodium acetoxyborohydride (1.27 g, 6.00 mmol) was added. After 1 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound as a solid (408 mg, 0.983 mmol, 98%).

Workup

  1. waitAfter 4 h
  2. waitAfter 30 min
  3. waitAfter 1 h
  4. customthe reaction mixture was quenched with water
  5. concentrationconcentrated in vacuo
  6. additiondiluted with ethyl acetate
  7. washwashed with aqueous sodium hydroxide (1 M) and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed9f7a0aacc340048f7bee19fb4e4c40
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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