Water → HCID 86227318, compound

HRID 1892501Notes

Reaction equation

HRID 1892501 reaction equation
N1([C:6]([C:8]2[S:12][C:11]([CH2:13][CH2:14][C:15]3[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=3)=[CH:10][CH:9]=2)=[O:7])C=CN=C1.O.[BH4-].[Na+]>O1CCCC1>[OH:7][CH2:6][C:8]1[S:12][C:11]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86650007HCID 86650007, compound

Product 1

HCID 86227318HCID 86227318, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(4-{2-[5-(1H-imidazol-1-ylcarbonyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (220.0 mg, 0.635 mmol) in anhydrous tetrahydrofuran (17.6 ml) was cooled to 0° C., and water (4.4 ml) and sodium borohydride (240.2 mg, 6.350 mmol) were added. After stirring at 0° C. for 1.5 hr, the reaction mixture was concentrated to about 2 ml, and saturated aqueous ammonium chloride (20 ml) was added dropwise. This was extracted 3 times with ethyl acetate, and the combined organic layer was washed with aqueous ammonium chloride and saturated brine. The mixture was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:1) to give N-(4-{2-[5-(hydroxymethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (157.1 mg, 0.556 mmol, yield 87.6%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated to about 2 ml, and saturated aqueous ammonium chloride (20 ml)
  2. additionwas added dropwise
  3. extractionThis was extracted 3 times with ethyl acetate
  4. washthe combined organic layer was washed with aqueous ammonium chloride and saturated brine
  5. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-03235402a6524f0e8510a87b1d48946f
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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