Sodium borohydride → HCID 178477644, compound

HRID 1671655Notes

Reaction equation

HRID 1671655 reaction equation
[BH4-].[Na+].[CH2:3]([S:5]([C:8]1[CH:35]=[CH:34][C:11]([O:12][C:13]2[C:14]([CH:28]([OH:33])[C:29]([O:31]C)=[O:30])=[CH:15][C:16]3[N:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[NH:18][C:17]=3[CH:27]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH3:4]>CO>[CH2:3]([S:5]([C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[C:14]([CH:28]([OH:33])[C:29]([OH:31])=[O:30])=[CH:15][C:16]3[N:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[NH:18][C:17]=3[CH:27]=2)=[CH:34][CH:35]=1)(=[O:6])=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178477645HCID 178477645, compound

Product 1

HCID 178477644HCID 178477644, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium borohydride (15 mg) was added to a methanol (1 ml) solution of methyl (6-(4-(ethylsulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)(hydroxy)acetate (21 mg) obtained in Example 31 (step 2), and the reaction liquid was stirred overnight at 60° C. The solvent was evaporated away under reduced pressure, and the reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid), and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline water in that order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe solvent was evaporated away under reduced pressure
  3. customthe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  4. additionthe resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound

Sources & evidence

ORD record
ord-6360223bbebe479d943468311ec7796c
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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