Triethylamine → 2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-6-iodo-8-methyl-4H-3,1-benzoxazin-4-one

HRID 254417노트

반응식

HRID 254417 반응식
CS(Cl)(=O)=O.[Cl:6][C:7]1[C:8]([N:13]2[C:17]([C:18]([OH:20])=O)=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[N:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C.[NH2:32][C:33]1[C:41]([CH3:42])=[CH:40][C:39]([I:43])=[CH:38][C:34]=1[C:35](O)=[O:36]>C(#N)C>[Cl:6][C:7]1[C:8]([N:13]2[C:17]([C:18]3[O:20][C:35](=[O:36])[C:34]4[CH:38]=[C:39]([I:43])[CH:40]=[C:41]([CH3:42])[C:33]=4[N:32]=3)=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[N:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chloride2회HCID 112312332-Amino-5-iodo-3-methylbenzoic AcidHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid2회

생성물 1

HCID 184469312-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-6-iodo-8-methyl-4H-3,1-benzoxazin-4-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매3회

반응 조건

온도
0 °C

실험 절차

To a solution of methanesulfonyl chloride (2.91 mL, 37.74 mmol) in acetonitrile (50 mL) was added dropwise a mixture of 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (i.e. the carboxylic acid product of Step C) (10.0 g, 34.31 mmol) and triethylamine (4.78 mL, 34.31 mmol) in acetonitrile (50 mL) at −5° C. The reaction temperature was then maintained at 0° C. throughout successive addition of reagents. After stirring for 20 minutes, 2-amino-3-methyl-5-iodobenzoic acid (i.e. the product from Step A) (9.51 g, 34.31 mmol) was added and stirring was continued for an additional 10 minutes. A solution of triethylamine (9.56 mL, 68.62 mmol) in acetonitrile (15 mL) was then added dropwise, and the reaction mixture was stirred 30 minutes, followed by the addition of methanesulfonyl chloride (2.91 mL, 37.74 mmol). The reaction mixture was then warmed to room temperature and stirred 2 hours. The solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford 8.53 g of the title compound as a yellow solid.

후처리

  1. stirringstirring
  2. waitwas continued for an additional 10 minutes
  3. stirringthe reaction mixture was stirred 30 minutes
  4. temperatureThe reaction mixture was then warmed to room temperature
  5. stirringstirred 2 hours
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residual solid was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-3675b64724374f509078c04a596a8837
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875634B2

반응 노트

불러오는 중…