Cyclopropylamine → HCID 22632896, compound

HRID 2270212Notes

Reaction equation

HRID 2270212 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[C:4]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[N:3]=1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>CC(N(C)C)=O.ClCCl>[CH:21]1([NH:24][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[C:4]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[N:3]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 22632876HCID 22632876, compound

Product 1

HCID 22632896HCID 22632896, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 2-chloro-5-fluoro-6-(4-methylpiperazinyl)-3-pyridine-carboxylate (Example D-2, 1.00 g, 3.314 mmol) and cyclopropylamine (2 mL) in DMA (1 mL) was sealed in a pressure bottle and heated at 90° C. for 60 hours. The reaction mixture was diluted with dichloromethane (30 mL), washed with water, and dried on sodium sulfate. Flash chromatography on silica gel column using dichloromethane as eluent provided compound 0.85 g of the title compound as an oil.

Workup

  1. washwashed with water
  2. customdried on sodium sulfate

Sources & evidence

ORD record
ord-12d9d1d815a840a38f39f4bb365dca18
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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