Butylamine → HCID 23498092, compound

HRID 1837334Notes

Reaction equation

HRID 1837334 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20]>C(OCCO)C>[CH2:17]([NH:21][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16])[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 121507034-Chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 23498092HCID 23498092, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile (300 mg, 1.27 mmol) and butylamine (205 mg, 2.80 mmol) in 10 mL of 2-ethoxyethanol is heated at 80° C. for 1.5 hours then cooled to room temperature. The reaction mixture is concentrated in vacuo and aqueous sodium bicarbonate is added to the residue. After stirring for 20 minutes, the solids are collected by filtration. Purification by preparative thin layer chromatography, eluting with 2% methanol in dichloromethane provides 230 mg of 4-butylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile, mp 155-156° C.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationThe reaction mixture is concentrated in vacuo and aqueous sodium bicarbonate
  3. additionis added to the residue
  4. filtrationthe solids are collected by filtration
  5. customPurification by preparative thin layer chromatography
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-a69c7fbb75f04b4e9c91c2181317344e
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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