Benzene → N-cyclopropyl-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250493Notes

Reaction equation

HRID 1250493 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([OH:22])=O)[CH:4]=1.S(Cl)(Cl)=O.C1C=CC=CC=1.[CH:33]1([NH2:36])[CH2:35][CH2:34]1>C(OCC)(=O)C.CN(C=O)C>[CH:33]1([NH:36][C:20]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=3)[N:6]=2)=[O:22])[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 109030764-Methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid

Product 1

HCID 15906605N-cyclopropyl-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.40 g (0.00128 mol) of 4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-picolinic acid was mixed with 0.3 g (0.00128×2.0 mol) thionyl chloride and then with about 10 ml of benzene and a small amount of DMF, followed by treating the obtained mixture under reflux for about 30 minutes. The reaction solution was concentrated and, thereafter, mixed with methylene chloride and then with 0.18 g (0.00128×2.5 mol) of cyclopropyl amine, followed by stirring at room temperature for about 30 minutes. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, and concentrated. Thereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. additionby treating the obtained mixture
  2. temperatureunder reflux for about 30 minutes
  3. concentrationThe reaction solution was concentrated
  4. additionmixed with methylene chloride
  5. washwashed with saturated brine
  6. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-59df4d196c7d48e685ccd44f429ffb9b
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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