反応 #2286384

反応方程式

3-methylsulfanyl-propionyl chloride

methyl-(2-pyridin-3-yl-thiazol-5-yl)-amine

→

powder

収率 75.0%

N-methyl-3-methylsulfanyl-N-(2-pyridin-3-yl-thiazol-5-yl)-propionamide

収率 75.0%

溶媒

DCE

DCE

DCE

反応条件

後処理

1. 1
   その他The ice bath was removed after 30 min
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   温度at reflux under nitrogen for 15 min
4. 4
   温度The reaction mixture was cooled
5. 5
   workup.ADDITIONdiluted with DCE (70 mL)
6. 6
   洗浄washed with saturated aqueous NaHCO3 (50 mL)
7. 7
   乾燥dried over MgSO4
8. 8
   その他purified by silica gel chromatography (3:1 ethyl acetate/hexanes)

実験手順

A solution of 3-methylsulfanyl-propionyl chloride (120 mg, 0.9 mmol) in DCE (1 mL) was pipetted at a dropwise rate into an ice-cold suspension of methyl-(2-pyridin-3-yl-thiazol-5-yl)-amine (114 mg, 0.6 mmol) in DCE (5 mL), and the mixture was stirred for 5 min before adding a solution of DMAP (80 mg, 0.6 mmol) in DCE (1 mL). The ice bath was removed after 30 min, and the mixture was stirred at reflux under nitrogen for 15 min. The reaction mixture was cooled, diluted with DCE (70 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and purified by silica gel chromatography (3:1 ethyl acetate/hexanes) to afford a fine yellow powder (131 mg, 75%): mp 116-118° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.0 Hz, 1H), 8.61 (dd, J=4.8, 1.4 Hz, 1H), 8.24 (dt, J=9.8, 1.8 Hz, 1H), 7.81 (s, 1H), 7.51 (dd, J=7.7, 4.7 Hz, 1H), 3.56 (s, 3H), 3.02 (t, J=7.0 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.12 (s, 3H); ESIMS m/z 294 (M+1).

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