Methanol → HCID 135681603, compound

HRID 1354649Notes

Reaction equation

HRID 1354649 reaction equation
C([O:3][C:4]([C:6]1[CH:32]=[CH:31][C:9]2[N:10]=[C:11]([C:13]3[C:14](=[O:30])[NH:15][CH:16]=[CH:17][C:18]=3[NH:19][CH2:20][CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[OH:22])[NH:12][C:8]=2[CH:7]=1)=O)C.[BH4-].[Na+].[CH3:35]O>C(O)(=O)C>[Cl:29][C:25]1[CH:24]=[C:23]([CH:21]([OH:22])[CH2:20][NH:19][C:18]2[CH:17]=[CH:16][NH:15][C:14](=[O:30])[C:13]=2[C:11]2[NH:12][C:8]3[CH:7]=[C:6]([CH2:4][OH:3])[CH:32]=[C:31]([CH3:35])[C:9]=3[N:10]=2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 136335184HCID 136335184, compound

Product 1

HCID 135681603HCID 135681603, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (±)-2-{4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}- -3H-benzimidazole-5-carboxylic acid ethyl ester (25 mg, 0,054 mmol) in methanol (2 mL) and acetic acid (1 mL) was added NaBH4 (10 mg, 0.27 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 30 min. and quenched with isopropanol (5 drops). After removal of most solvent, the residue was extracted with EtOAc, washed with water and brine, dried over Na2SO4. After concentration, the crude product was purified by prep. HPLC to yield the title compound (18 mg, 62%). 1H NMR (300 MHz, CD3OD) δ 7.50 (1H, s), 7.48 (1H, s), 7.25–7.38 (4H, m), 7.22 (1H, s), 6.25 (1H, d, J=7.6 Hz), 4.89–4.94 (1H, m), 4.76 (2H, s), 3.51–3.62 (2H, m), 2.62 (3H, s). LCMS (M+H)+ m/z 425 (t=1.64 min.).

Workup

  1. customquenched with isopropanol (5 drops)
  2. customAfter removal of most solvent
  3. extractionthe residue was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe crude product was purified by prep

Sources & evidence

ORD record
ord-36bb41788eb342fca3217c5a0d0b7dcc
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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