반응 #584765

반응 방정식

monoethyl fumarate

6-chloro-1H-indazole-3-amine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

Ethyl (2E) 4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoate

용매

dichloromethane

반응 조건

후처리

1. 1
   세척The resulting mixture is washed with 50 cm3 of distilled water
2. 2
   건조The organic phase is dried over magnesium sulphate
3. 3
   여과filtered
4. 4
   기타evaporated under reduced pressure (2 kPa; 40° C.)
5. 5
   기타2 g of a brick-coloured gummy mass are obtained
6. 6
   기타are purified by chromatography under an argon pressure of 50 kPa
7. 7
   세척on a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (90/10 by volume)
8. 8
   기타collecting 40 cm3 fractions
9. 9
   workup.ADDITIONThe fractions containing the expected product
10. 10
    기타evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C
11. 11
    건조After drying (90 Pa; 45° C.), 900 mg of ethyl 4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoate, (E form), melting at 220° C.
12. 12
    기타are obtained

실험 절차

865 mg of monoethyl fumarate are added to 1 g of 6-chloro-1H-indazole-3-amine in 50 cm3 of dichloromethane. 1.4 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are then introduced and the mixture is stirred for 30 minutes at about 20° C. The resulting mixture is washed with 50 cm3 of distilled water and then with 50 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and then evaporated under reduced pressure (2 kPa; 40° C.). 2 g of a brick-coloured gummy mass are obtained, and are purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (90/10 by volume) and collecting 40 cm3 fractions. The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. After drying (90 Pa; 45° C.), 900 mg of ethyl 4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoate, (E form), melting at 220° C., are obtained.

출처