반응 #45238

반응 방정식

naphthalene-2-carboxylic acid

solution

3-[3-(5-amino-3-t-butyl-pyrazol-1-yl)-phenyl]-propionic acid ethyl ester

→

3-(3-{3-t-butyl-5-[(naphthalene-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

수율 38.3%

용매

SOCl2

CH2Cl2

반응 조건

후처리

1. 1
   온도to reflux for 2 h
2. 2
   농축After concentration under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved into CH2Cl2 (5 mL)
4. 4
   기타After quenching with water (50 mL)
5. 5
   추출the reaction mixture was extracted with CH2Cl2 (3×100 mL)
6. 6
   세척The combined organic extracts were washed with brine
7. 7
   건조dried (NaSO4)
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타to yield a residue which
11. 11
    기타was purified by flash chromatography

실험 절차

A solution of naphthalene-2-carboxylic acid (344 mg, 2.0 mmol) in SOCl2 (10 mL) was heated to reflux for 2 h. After concentration under reduced pressure, the residue was dissolved into CH2Cl2 (5 mL) and was dropped into a solution of Example Z (315 mg, 1.0 mmol) in CH2Cl2 (10 mL) at 0° C., and was then stirred at RT overnight. After quenching with water (50 mL), the reaction mixture was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried (NaSO4), filtered and concentrated under reduced pressure to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[(naphthalene-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester (180 mg, 38%). 1H-NMR (CDCL3): 8.24 (s, 1H), 8.21 (s, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.88 (d, J=8.4 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.63-7.49 (m, 3H), 7.45-7.26 (m, 3H), 6.94 (s, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.04 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 1.43 (s, 9H), 1.17 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 470 (M+H+).

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