Sodium borohydride → HCID 178513580, compound

HRID 2247155Notes

Reaction equation

HRID 2247155 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([NH2:26])=[O:25])=[CH:23][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([NH2:26])=[O:25])=[CH:23][C:17]=3[N:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178513579HCID 178513579, compound

Product 1

HCID 178513580HCID 178513580, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-benzoyl-phenyl)-1H-benzoimidazole-5-carboxylic acid amide (Example 3, 18 mg, 0.05 mmol) in anhydrous methanol (2.0 mL) was added sodium borohydride (2.0 mg, 0.05 mmol) in one portion. The reaction mixture was stirred under N2 for 1 h. The solvent was removed under reduced pressure, and the residue was re-dissolved in 1:1 ethyl acetate/H2O (40 mL). The solution was washed with H2O (20 mL) then brine (20 mL) and dried (Na2SO4). Solvent was removed under reduced pressure, and purification by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 15 mg (83%) of the title compound. TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2): Rf=0.13. HPLC (Method A): Rt=6.36. MS (ESI+): mass calculated for C21H17N3O2, 343.1; m/z found, 344.1 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.17 (br s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.82-7.80 (dd, J=8.4, 1.4 Hz, 1H), 7.63 (br d, J=6.7 Hz, 1H), 7.58 (d, J=8.2 Hz, 2H), 7.42-7.40 (dd, J=8.5, 1.4 Hz, 2H), 7.32 (t, =J=7.5 Hz, 2H), 7.26-7.22 (m, 1H), 5.85 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was re-dissolved in 1:1 ethyl acetate/H2O (40 mL)
  3. washThe solution was washed with H2O (20 mL)
  4. dry with materialbrine (20 mL) and dried (Na2SO4)
  5. customSolvent was removed under reduced pressure, and purification by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-2970f3ea87284c95b34bfab5f8cdfa77
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

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