Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-methoxy-amide

HRID 241502노트

반응식

HRID 241502 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[NH:12][O:13][CH3:14])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:22][CH:23]([F:33])[C:24]1[C:28]([C:29](Cl)=[O:30])=[CH:27][N:26]([CH3:32])[N:25]=1>ClCCl.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[N:12]([O:13][CH3:14])[C:29]([C:28]2[C:24]([CH:23]([F:33])[F:22])=[N:25][N:26]([CH3:32])[CH:27]=2)=[O:30])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 86699875N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine

생성물 1

HCID 866998743-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-methoxy-amide수율 91.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
22 °C

실험 절차

To a stirred solution of N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine (0.60 g; 2.80 mmol), prepared as described in example P1b and triethylamine (0.80 ml; 5.70 mmol) in dichloromethane (10 ml) under nitrogen at 15° C. was added dropwise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.545 g; 2.80 mmol) in dichloromethane (5 ml). The reaction mixture was stirred at 22° C. for 14 h under nitrogen. The mixture was poured in water and extracted three times with dichloromethane. Combined organics were dried over sodium sulfate and the solvent was removed in vacuo. The crude was subject to flash chromatography (eluant: c-hexane/ethyl acetate 60:40) to afford 0.95 g (91% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-methoxy-amide as a yellow oil, that crystallized.

후처리

  1. extractionextracted three times with dichloromethane
  2. dry with materialCombined organics were dried over sodium sulfate
  3. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-a8c5032f725c45e2a8e529921bec0eda
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653003B2

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