Cyclopropylamine → 2-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

HRID 1734123Notes

Reaction equation

HRID 1734123 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]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 104236502-Chloro-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

Product 1

HCID 104474082-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamideYield 86%

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).

Workup

  1. customRemoval of the cyclopropylamine
  2. customby rotary evaporation

Sources & evidence

ORD record
ord-b74d61fbe4d743d8934a5c97d9ac0506
Source dataset
uspto-grants-1996_07
Patent number
US05532358

Reaction notes

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