Sodium borohydride → HCID 22181282, compound

HRID 1796507Notes

Reaction equation

HRID 1796507 reaction equation
[CH2:1]([O:3][C:4]1[CH:32]=[CH:31][C:7]([C:8]([C:10]2[N:14]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]3[CH:20]=[CH:21][C:22]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])=[CH:23][C:12]=3[N:11]=2)=[O:9])=[CH:6][CH:5]=1)[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([O:3][C:4]1[CH:32]=[CH:31][C:7]([CH:8]([OH:9])[C:10]2[N:14]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]3[CH:20]=[CH:21][C:22]([C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])=[CH:23][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22181310HCID 22181310, compound

Product 1

HCID 22181282HCID 22181282, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-ethoxybenzoyl)-N,N-diethyl-1-(3-methylbutyl)-1H-benzimidazole-5-carboxamide (110 mg, 0.252 mmol) was dissolved in 3 mL of EtOH. NaBH4 (12 mg, 1.2 eq) was added and the solution stirred at rt for 1 h. The solvent was concentrated and the residue dissolved in EtOAc. The organic phase was washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was directly purified by reversed-phase chromatography (C-18 column) using a gradient of 10–65% CH3CN/H2O and then lyophilized affording the title compound. The product was isolated as the corresponding TFA salt. Yield: 102 mg (73%); 1H NMR (400 MHz, CD3OD) δ 7.85 (br s, 2H), 7.62 (br s, 1H), 7.40 (br s, 2H), 7.01 (br s, 2H), 6.33 (br s, 1H), 4.29 (br s, 2H), 4.06 (br s, 2H), 3.62 (br s, 2H), 3.32 (br s, 2H), 1.55 (br, 2H), 1.38 (br s, 3H), 1.30 (br s, 3H), 1.17 (br s, 2H), 0.90 (s, 3H), 0.83 (s, 3H); MS (ESI) (M+H)+=438.30; Anal. Calcd for C26H35N3O3+1.2 TFA: C, 59.38; H, 6.35; N, 7.32. Found: C, 59.36; H, 5.97; N, 7.37.

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with saturated NaHCO3 solution, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was directly purified by reversed-phase chromatography (C-18 column)

Sources & evidence

ORD record
ord-dbb0ffb75592418193645bc6fc58cd50
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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