Tetrahydrofuran → N1-Cyclopropyl-5-({2-[di(cyclopropylcarbonyl)amino]-4-pyridyl}oxy)-1H-1-indolecarboxamide

반응식

[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH:7]1([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH2:9][CH2:8]1.C(N(CC)CC)C.[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH:7]1([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([N:29]([C:41]([CH:40]5[CH2:38][CH2:39]5)=[O:37])[C:4]([CH:1]5[CH2:3][CH2:2]5)=[O:5])[CH:24]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH2:9][CH2:8]1

참가 물질

반응물 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 77637Cyclopropanecarbonyl chloride

HCID 21949236N1-cyclopropyl-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamide

생성물 1

HCID 22936650N1-Cyclopropyl-5-({2-[di(cyclopropylcarbonyl)amino]-4-pyridyl}oxy)-1H-1-indolecarboxamide

실험 절차

Cyclopropanecarbonyl chloride (51 mg) was added to a solution of 100 mg of N1-cyclopropyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide and 49 mg of triethylamine in tetrahydrofuran at 0° C. After 20 minutes of stirring, silica gel was added to the reaction solution, the solvent was distilled off under reduced pressure, and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate), after which water was added to the residue to obtain 19 mg of the target substance as a white solid.