Citric Acid → 4-Hydroxy-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide

HRID 1851551Notes

Reaction equation

HRID 1851551 reaction equation
[O:1]=[C:2]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)=[CH:13]2)=[O:6].O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[OH:1][CH:2]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)=[CH:13]2)=[O:6]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 579017094-Oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide

Product 1

HCID 579016334-Hydroxy-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide (1.43 g), tetrahydrofuran (10 ml) and methanol (10 ml) was added sodium borohydride (0.16 g) at 0° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (1.21 g, yield 84%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. melting point 155-157° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5dacf5a69ffc48f1abad29883ec9e663
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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