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

HRID 241502Notes

Reaction equation

[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

Participants

Conditions

Temperature: 22 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a8c5032f725c45e2a8e529921bec0eda
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653003B2

Reaction notes

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