반응 #547438

반응 방정식

6-(piperidylmethyl)-2-pyridylamine

2-(3-methoxyphenyl)-1,3-thiazole-4-carboxylic acid

EtOAc

(PhO)2PON3

→

title compound

1-[2-(3-Methoxyphenyl)thiazol-4-yl]-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

용매

toluene

반응 조건

후처리

1. 1
   온도The resulting mixture was heated
2. 2
   온도at reflux for 4 h
3. 3
   온도The mixture was cooled to RT
4. 4
   농축concentrated by rotary evaporation
5. 5
   기타purified on silica gel (5:95 MeOH/CH2Cl2)
6. 6
   기타The yellow solid obtained
7. 7
   세척washed with a saturated solution of NH4Cl (aq)
8. 8
   기타The organic phase was separated
9. 9
   건조dried over MgSO4
10. 10
    여과filtered
11. 11
    농축concentrated by rotary evaporation
12. 12
    기타The product was recrystallized from hexanes

실험 절차

To a stirred solution of 2-(3-methoxyphenyl)-1,3-thiazole-4-carboxylic acid (0.17 g, 0.72 mmol) in toluene (10 mL) at RT and under N2 was added TEA (0.2 mL). After 5 min, (PhO)2PON3 (0.2 5 mL) was added and the reaction mixture was heated at 85° C. for 20 min followed by the addition of 6-(piperidylmethyl)-2-pyridylamine (0.21 g, 1.1 mmol). The resulting mixture was heated at reflux for 4 h using a Dean-Stark trap. The mixture was cooled to RT, concentrated by rotary evaporation and purified on silica gel (5:95 MeOH/CH2Cl2). The yellow solid obtained was dissolved in EtOAc (15 mL) and washed with a saturated solution of NH4Cl (aq). The organic phase was separated, dried over MgSO4, filtered and concentrated by rotary evaporation. The product was recrystallized from hexanes to afford the title compound as a white solid. EI-MS m/z 424 (M+H). Calc'd for C22H25N5O2S: 423.17.

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