Methanol → HCID 71819026, compound

HRID 1097489Notes

Reaction equation

HRID 1097489 reaction equation
[BH4-].[Na+].CO.[C:5]([C:7]1[C:15]2[S:14][C:13]([NH:16][C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])=[N:12][C:11]=2[CH:10]=[CH:9][C:8]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([NH:30]C(=O)C(F)(F)F)[CH:24]=1)#[N:6]>C(O)C>[NH2:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[F:29])[O:22][C:8]1[CH:9]=[CH:10][C:11]2[N:12]=[C:13]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21]3)=[O:18])[S:14][C:15]=2[C:7]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 71819025HCID 71819025, compound

Product 1

HCID 71819026HCID 71819026, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of sodium borohydride (586 mg, 15.5 mmol) in ethanol (7 mL) was added dropwise methanol (3 ml). To this suspension was added N-(7-cyano-6-{4-fluoro-3-[(trifluoroacetyl)amino]phenoxy}-1,3-benzothiazol-2-yl)cyclopropanecarboxamide (360 mg, 0.775 mmol). The reaction mixture was stirred at 60° C. for 1 hr, cooled to room temperature, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=80/20→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (194 mg, 68%) as a white powder.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate (100 mL)
  4. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationInsoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=80/20→100/0)
  9. concentrationthe obtained solution was concentrated under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-2e4f49cb777f42a5b6fcc450d096d89f
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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