Water → HCID 67119277, compound

HRID 1189002Notes

Reaction equation

HRID 1189002 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18](OCC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+].O>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][N:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][CH2:18][OH:19])[CH2:15][N:16]=1)=[CH:8]2

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 66898360HCID 66898360, compound

Product 1

HCID 67119277HCID 67119277, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [2-(7-methoxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (270 mg) was dissolved in a mixture of tetrahydrofuran (3 mL) and methanol (1.5 mL). Lithium borohydride (62 mg) was added to the mixture at 0° C. and the mixture was stirred at room temperature for 4 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio), followed by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/20/80 to 10/90/0) to give the title compound (110 mg, 43%) as a white amorphous solid. MS 448 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio)

Sources & evidence

ORD record
ord-1304f984360046ae9ae53d9c117c751e
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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