Cyclopropylamine → HCID 22633001, compound

HRID 2416820Notes

Reaction equation

HRID 2416820 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[CH2:18][CH2:17][CH2:16][CH2:15]2)[N:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>CC(N(C)C)=O.ClCCl>[CH:19]1([NH:22][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[CH2:18][CH2:17][CH2:16][CH2:15]3)[N:3]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 22632890HCID 22632890, compound

Product 1

HCID 22633001HCID 22633001, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 2-chloro-5-fluoro-6-pyrrolidinyl-3-pyridinecarboxylate (Example C-2, 500 mg, 1.83 mmol) and cyclopropylamine (2 mL) in DMA (1 mL) was sealed in a pressure bottle and heated at 90° C. for 1 day. The reaction mixture was diluted with dichloromethane (40 mL), washed with water, and dried on sodium sulfate. Flash chromatography on a silica gel column using dichloromethane/hexane (3:2) as eluent provided 270 mg of the title compound as an oil.

Workup

  1. washwashed with water
  2. customdried on sodium sulfate

Sources & evidence

ORD record
ord-4cc7ee6e03f344758e5f41d0710c45dd
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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