Triethylamine → HCID 57435625, compound

HRID 900048Notes

Reaction equation

[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12](Cl)=[O:13].[CH3:15][CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>O1CCCC1>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([NH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH:16]([CH3:15])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

At from 0° C. to −10° C., a solution comprising 8.1 g (42.4 mmol) of 5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride in 80 ml of tetrahydrofuran is added dropwise to a solution comprising 6.5 g (28.3 mmol) of 2-(1,3,3-trimethylbutyl)phenylamine and 5.7 g (56.6 mmol) of triethylamine in 200 ml of tetrahydrofuran. The reaction mixture is stirred at 0° C. for 1 h. For work-up, the mixture is filtered through silica gel and concentrated. Purification on silica gel (petroleum ether/ethyl acetate 3:1) gives 10.1 g (94% of theory) of [5-fluoro-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]-N-[2-(1,3,3-trimethylbutyl)phenyl]carbox-amide of log P (pH 2.3)=4.14.

Workup

filtrationFor work-up, the mixture is filtered through silica gel
concentrationconcentrated
customPurification on silica gel (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record: ord-0e992073e1c14cee9add4a8287ba6b4e
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358214B2

Reaction notes

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