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

HRID 642580

반응식

HRID 642580 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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 solids were collected
  6. washwashed with ether
  7. customThe solids were air-dried
  8. customdried in vacuo at 90° C. for 5 h

출처 및 근거

ORD 기록
ord-6c9a174fab244adba909f5ea0f9c19fb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696233B2

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