Reaction #792157

Reaction equation

benzoxazinone

2-[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one

isopropylamine

diethyl ether

→

title compound

Yield 87.3%

1-(3-Chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)-amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Yield 87.3%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONthe suspension thinned during the addition
2. 2
   TemperatureThe reaction mixture was then warmed
3. 3
   Temperatureto reflux for 1.5 h
4. 4
   OtherA new suspension formed
5. 5
   OtherThe solids were collected
6. 6
   Washwashed with ether
7. 7
   OtherThe solids were air-dried
8. 8
   Otherdried in vacuo at 90° C. for 5 h

Procedure

To a suspension of the benzoxazinone product of Step D (124 g, 300 mmol) in dichloromethane (500 mL) was added dropwise isopropylamine (76 mL, 900 mmol) at room temperature. The temperature of the reaction mixture rose and the suspension thinned during the addition. The reaction mixture was then warmed to reflux for 1.5 h. A new suspension formed. The reaction mixture was cooled to room temperature and diethyl ether (1.3 L) was added and the mixture stirred at room temperature overnight. The solids were collected and washed with ether. The solids were air-dried and then dried in vacuo at 90° C. for 5 h to yield 122 g of the title compound, a compound of the present invention, as a fluffy white solid, melting at 194-196° C.

Source