Acetyl chloride → HCID 86644706, compound

HRID 1097514Notes

Reaction equation

HRID 1097514 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[CH:17][C:18]([F:36])=[C:19]([NH:21][C:22](=[O:35])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([C:32]#[N:33])([CH3:31])[CH3:30])[C:24]=4[Cl:34])[CH:20]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:37](Cl)(=[O:39])[CH3:38]>N1C=CC=CC=1>[C:37]([NH:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[CH:17][C:18]([F:36])=[C:19]([NH:21][C:22](=[O:35])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([C:32]#[N:33])([CH3:31])[CH3:30])[C:24]=4[Cl:34])[CH:20]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86644705HCID 86644705, compound

Product 1

HCID 86644706HCID 86644706, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{5-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide (199 mg, 0.38 mmol) in pyridine (2 mL) was added acetyl chloride (41 μL, 0.57 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate (50 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 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=60/40→100/0), and the obtained solution was concentrated under reduced pressure to give the title compound (125 mg, 58%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (50 mL)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 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 basic silica gel column chromatography (ethyl acetate/n-hexane=60/40→100/0)
  8. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f173ca0bbfb7467d98dad020997316c7
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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