Cyclopropylamine → 2-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>>[CH:20]1([NH:23][C:2]2[C:7]([C:8]([NH:10][C:11]3[C:12]([O:18][CH3:19])=[N:13][CH:14]=[CH:15][C:16]=3[CH3:17])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:22][CH2:21]1Participants
3
Conditions
- Temperature
- 110 °C
Procedure
2-Chloro-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (0.55 g, 2 mmol) was placed in a sealed tube containing cyclopropylamine (0.5 mL, 7 mmol) and heated to 110° C. overnight. Removal of the cyclopropylamine by rotary evaporation followed by flash chromatography of the residue on silica gel (1:1 EtOAc:hexanes) gave the desired compound in 86% yield (0.51 g). m.p.: 151°-152° C. (Recrystallized from heptane).