Cyclopropylamine → HCID 18466610, compound

HRID 2229330Notes

Reaction equation

HRID 2229330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([NH:11][C:12]2[C:13]([Cl:20])=[N:14][C:15]([Cl:19])=[CH:16][C:17]=2[CH3:18])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([NH:11][C:12]2[C:13]([Cl:20])=[N:14][C:15]([Cl:19])=[CH:16][C:17]=2[CH3:18])=[O:10])[C:5]([NH:24][CH:21]2[CH2:23][CH2:22]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 18466614HCID 18466614, compound

Product 1

HCID 18466610HCID 18466610, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-2-chloro-N-(2,6-dichloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (3.00 g, 7.61 mmol) and cyclopropylamine (2.11 mL, 30.5 mmol) in xylenes was heated in a sealed tube at 120° C. for 24 h. The reaction was cooled to 0° C., diluted with water and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by trituration (Et2O:hexane, 3:1) to give the title compound (2.35 g, 75% yield) as a pale yellow solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by trituration (Et2O:hexane, 3:1)

Sources & evidence

ORD record
ord-3d8dbda2bf32418b8fafdd878830094b
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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