Methanol → HCID 86644695, compound

HRID 1097495Notes

Reaction equation

HRID 1097495 reaction equation
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[S:10][C:11]2[C:17]([C:18]#[N:19])=[C:16]([O:20][C:21]3[CH:22]=[CH:23][C:24]([F:34])=[C:25]([NH:27]C(=O)C(F)(F)F)[CH:26]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1)(=[O:7])[CH3:6]>C(O)C>[NH2:27][C:25]1[CH:26]=[C:21]([CH:22]=[CH:23][C:24]=1[F:34])[O:20][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([NH:8][C:5](=[O:7])[CH3:6])[S:10][C:11]=2[C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86644694HCID 86644694, compound

Product 1

HCID 86644695HCID 86644695, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium borohydride (3.0 g, 79.4 mmol) in is ethanol (30 mL) was added dropwise methanol (6 mL). To this suspension was added N-(5-{[2-(acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}-2-fluorophenyl)-2,2,2-trifluoroacetamide (700 mg, 1.60 mmol). The reaction mixture was stirred at room temperature for 20 min, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (150 mL), washed successively with saturated 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 silica gel column chromatography (ethyl acetate/n-hexane=50/50→100/0). The obtained solution was concentrated under reduced pressure to give the title compound (260 mg, 48%) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (150 mL)
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=50/50→100/0)
  8. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c80aa033b4934b45a392b32a7dd45837
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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