반응 #86048

반응 방정식

methyl 4-(8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

cyclopentyl bromide

cesium carbonate

→

solid

수율 45.0%

methyl 4-(8-(1-cyclopentyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

수율 45.0%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   세척the resulting solution was washed with saturated aqueous sodium chloride solution
2. 2
   농축The collected organic was concentrated
3. 3
   기타Purification of the resulting residue by flash column chromatography (20% ethyl acetate in dichloromethane)

실험 절차

A suspension of methyl 4-(8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (43 mg, 0.13 mmol, 1 equiv), cyclopentyl bromide (41 μL, 0.38 mmol, 3.0 equiv) and cesium carbonate (126 mg, 0.383 mmol, 3.0 equiv) in N,N-dimethylformamide (1 mL) was heated at 100° C. After 2 h, the reaction mixture was diluted with ethyl acetate, and the resulting solution was washed with saturated aqueous sodium chloride solution. The collected organic was concentrated. Purification of the resulting residue by flash column chromatography (20% ethyl acetate in dichloromethane) afforded a white solid (23.5 mg, 45% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.18 (s, 1H), 8.74-8.55 (m, 2H), 8.32 (s, 1H), 7.91 (dd, J=13.9, 8.1 Hz, 3H), 7.85 (d, J=8.9 Hz, 2H), 7.10 (t, J=7.0 Hz, 1H), 4.81 (s, 1H), 3.82 (s, 3H), 2.25-2.11 (m, 2), 2.11-1.93 (m, 2H), 1.85 (d, J=3.5 Hz, 2H), 1.77-1.63 (m, 2H).

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