Sodium borohydride → HCID 59267787, compound

HRID 1945305Notes

Reaction equation

HRID 1945305 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH2:33][CH2:34][OH:35])[CH:28]=[CH:27]3)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:22])=[C:17]([CH:21]=3)[C:18]([OH:20])=[O:19])[NH:9][C:8]=2[CH:23]=1>CC(O)=O>[Cl:3][C:4]1[C:5]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH2:33][CH2:34][OH:35])[CH2:28][CH2:27]3)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:22])=[C:17]([CH:21]=3)[C:18]([OH:20])=[O:19])[NH:9][C:8]=2[CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59267834HCID 59267834, compound

Product 1

HCID 59267787HCID 59267787, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

NaBH4 (22 mg, 0.585 mmol) was added to a solution of 5-({6-chloro-5-[1-(2-hydroxyethyl)-1H-indol-5-yl]-1H-benzimidazol-2-yl}oxy)-2-methylbenzoic acid (30 mg, 0.065 mmol, Example 263) in AcOH (1 mL). The reaction was maintained overnight at ambient temperature, quenched with 2 N aqueous HCl and concentrated. The residue was partitioned between EtOAc and H2O. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Purification of the resulting residue by reverse phase HPLC eluting with 35-100% MeCN/water) afforded the title compound. LC-MS: calculated for C25H22ClN3O4 463.91, observed m/e 464.3 (M+H)+ (Rt 1.60 min).

Workup

  1. customquenched with 2 N aqueous HCl
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and H2O
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resulting residue by reverse phase HPLC
  10. washeluting with 35-100% MeCN/water)

Sources & evidence

ORD record
ord-18a0d9bb3af1490e83e530328a780c95
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

Loading…