تفاعل #2286384

معادلة التفاعل

3-methylsulfanyl-propionyl chloride

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

→

powder

المردود 75.0%

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

المردود 75.0%

المذيبات

DCE

DCE

DCE

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice bath was removed after 30 min
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   درجة الحرارةat reflux under nitrogen for 15 min
4. 4
   درجة الحرارةThe reaction mixture was cooled
5. 5
   workup.ADDITIONdiluted with DCE (70 mL)
6. 6
   غسيلwashed with saturated aqueous NaHCO3 (50 mL)
7. 7
   تجفيفdried over MgSO4
8. 8
   أخرىpurified by silica gel chromatography (3:1 ethyl acetate/hexanes)

الإجراء التجريبي

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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