Reaktion #339888

Reaktionsgleichung

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

Triethylamine

acetyl chloride

→

title product

Ausbeute 91.0%

N-{5-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-2-chloro pyridin-3-yl}-N-(phenylsulfonyl)acetamide

Ausbeute 91.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was placed in an ice-bath
2. 2
   Sonstigeevaporated
3. 3
   workup.ADDITIONWater and ethyl acetate were added
4. 4
   TrocknenThe organic phase was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe reaction product was purified by preparative HPLC (Method A)

Vorschrift

N-{5-[6-Chloro-5-(phenylsulfonylamino)pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl)acetamide was dissolved in THF. Triethylamine (0.113 mL, 0.811 mmol) was added. The solution was placed in an ice-bath and acetyl chloride (0.058 mL, 0.81 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours and then evaporated. Water and ethyl acetate were added. The organic phase was dried with magnesium sulfate, filtered and evaporated. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 9.2 minutes) in 91% yield; 1H NMR Spectrum: (DMSOd6) 12.33 (1H, s); 8.69 (1H, d); 8.24 (1H, d); 8.06-8.00 (2H, m); 7.82 (1H, t); 7.72-7.67 (2H); 2.42 (3H, s); 2.17 (3H, s); 1.96 (3H, s); Mass Spectrum: M+H+ 465 and 467.

Quelle