Reaktion #339894

Reaktionsgleichung

2,4-Dimethoxyphenylsulfonyl chloride

N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

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title compound

Ausbeute 27.3%

N-{5-[6-Chloro-5-(2,4-dimethoxyphenylsulfonylamino)pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide

Ausbeute 27.3%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated by evaporation
2. 2
   SonstigeThe residue was purified by preparative HPLC on Kromasil C18 reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent at a flow rate of about 10 mL/minute
3. 3
   SonstigeThe material so obtained
4. 4
   Sonstigewas triturated under diethyl ether

Vorschrift

2,4-Dimethoxyphenylsulfonyl chloride (J. Med. Chem., 1977, 20, 1235; 376 mg) was added to a stirred solution of N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (150 mg) in pyridine (1.5 mL) and the resultant solution was heated at 50° C. for 16 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC on Kromasil C18 reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent at a flow rate of about 10 mL/minute. The material so obtained was triturated under diethyl ether to give the title compound as a white solid (70 mg); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.29 (s, 3H), 3.76 (s, 3H), 3.83 (s, 3H), 6.60 (m, 1H), 6.69 (d, 1H), 9.64 (d, 1H), 6.75 (d, 1H), 8.25 (br s, 1H), 9.80 (s, 1H); Mass Spectrum: M+H+ 483.

Quelle