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

HRID 475457

Reaction equation

HRID 475457 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:18][C:17](=[O:19])[C:16]4[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:15]=4[N:14]=3)=[CH:11][C:10]([C:25]([F:28])([F:27])[F:26])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:29]([NH2:32])([CH3:31])[CH3:30].C(OCC)C>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([NH:14][C:15]3[C:16]([C:17]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:19])=[CH:20][CH:21]=[CH:22][C:23]=3[CH3:24])=[O:18])=[CH:11][C:10]([C:25]([F:27])([F:26])[F:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6363IsopropylamineHCID 231503482-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one

Product 1

HCID 102985871-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamideYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. additionthe suspension thinned during the addition
  2. temperatureThe reaction mixture was then warmed
  3. temperatureto reflux for 1.5 h
  4. customA new suspension formed
  5. customThe reaction, mixture
  6. customThe solids were collected
  7. washwashed with ether
  8. customThe solids were air-dried
  9. customdried in vacuo at 90° C. for 5 h

Sources & evidence

ORD record
ord-336f214e989a43eda5c25c3664286b0d
Source dataset
uspto-grants-2014_01
Patent number
US08637552B2

Linked notes

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