反应 #2314349

反应方程式

ethyl 4-hydroxy-6-iodo-7-methyl[1,8]naphthyridine-3-carboxylate

4-chlorobenzylamine

→

desired product

收率 58.0%

N-(4-chlorobenzyl)-4-hydroxy-6-iodo-7-methyl[1,8]naphthyridine-3-carboxamide

收率 58.0%

溶剂

Ethyl acetate

—

hexanes

反应条件

后处理

1. 1
   过滤the solid is filtered
2. 2
   洗涤washed thoroughly with hexanes
3. 3
   其他dried
4. 4
   workup.DISSOLUTIONThe crude solid is dissolved in CH2Cl2/MeOH
5. 5
   其他Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (3L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L))

实验过程

A solution of ethyl 4-hydroxy-6-iodo-7-methyl[1,8]naphthyridine-3-carboxylate Prep 4(0.41 g) and 4-chlorobenzylamine (2.50 mL) is heated at 180° C. for 1 h. The reaction is cooled to room temperature. Ethyl acetate (10 mL) and then hexanes (20 mL) are added and the solid is filtered, washed thoroughly with hexanes, and dried. The crude solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (3L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L)) affords the desired product as a white solid (0.30 g, 0.66 mmol, 58%). Physical characteristics are as follows: m.p. 276-277° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.17, 10.10, 8.83, 8.66, 7.40, 7.35, 4.54, 2.77; IR (drift) 3063, 3022, 2957, 2895, 1650, 1596, 1552, 1521, 1493, 1405, 1352, 1323, 1241, 1095, 807 cm−1; MS (ESI) m/z 453.6 (M+H)+, 451.7 (M−H)−; Anal. Calcd for C17H13ClIN3O2: C, 45.01; H, 2.89; N, 9.26; Found: C, 44.92; H, 2.78; N, 9.17.

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