Pyridine → N-(5-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}-2-methylphenyl)-3-(1-cyano-1-methylethyl)benzamide

HRID 2190481Notes

Reaction equation

HRID 2190481 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:28])[CH3:27])[CH:21]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[C:39](Cl)(=[O:41])[CH3:40]>O1CCCC1.C(OCC)(=O)C>[C:39]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:27])[CH3:28])[CH:21]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86646002N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 58349026N-(5-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}-2-methylphenyl)-3-(1-cyano-1-methylethyl)benzamideYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (200 mg, 0.452 mmol) produced in Example A7(vii) in tetrahydrofuran (2.0 mL) were added pyridine (180 μL, 2.25 mmol) and acetyl chloride (51 μL, 0.723 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (20 mL), washed with 5% aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from 2-butanone/hexane to give the title compound (138 mg, 63%) as colorless crystals.

Workup

  1. washwashed with 5% aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL)
  2. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  6. concentrationthe obtained solution was concentrated under reduced pressure
  7. customThe residue was recrystallized from 2-butanone/hexane

Sources & evidence

ORD record
ord-d4334725f66e43479bab51c8dd57454b
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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