Hydrazine → HCID 59632585, compound

HRID 2369067Notes

Reaction equation

[F:1][C:2]([F:24])([F:23])[C:3](=O)[CH2:4][C:5]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)=[CH:10][CH:11]=1)=O.[NH2:25][NH2:26]>C1(C)C=CC=CC=1>[CH3:21][S:18]([C:14]1[CH:13]=[C:12]([C:9]2[S:8][C:7]([C:5]3[CH:4]=[C:3]([C:2]([F:24])([F:23])[F:1])[NH:26][N:25]=3)=[CH:11][CH:10]=2)[CH:17]=[CH:16][CH:15]=1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 100 mL flask was weighed 5.18 g (13.8 mmol) of 4,4,4-Trifluoro-1-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-butane-1,3-dione, 50 mL of toluene, and 450 μL (14.3 mmol) of hydrazine. The resulting solution was heated at 100° C. for 21 h. The reaction was then concentrated in vacuo and was partially purified by silica gel flash chromatography (Jones Flashmaster, 70 g SiO2, gradient elution from 100% hexanes to 20% ethyl acetate over 30 minutes. Appropriate fractions were combined, concentrated in vacuo, and were precipitated from ethyl acetate with hexanes to afford the intermediate 3-[5-(3-Methanesulfonyl-phenyl)-thiophen-2-yl]-5-trifluoromethyl-1H-pyrazole as a faintly yellow, semi-crystalline solid, yield: 1.24 g (24%). 1H NMR (400 MHz, CDCl3): δ 8.15 (s, 1H), 7.86 (d, J=8 Hz, 2H), 7.62 (t, J=8 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.39 (d, J=4 Hz, 1H), 6.70 (s, 1H), 3.12 (s, 3H); MS (ES): 373 [M+H]+.

Workup

customInto a 100 mL flask was weighed
concentrationThe reaction was then concentrated in vacuo
customwas partially purified by silica gel flash chromatography (
washJones Flashmaster, 70 g SiO2, gradient elution from 100% hexanes to 20% ethyl acetate over 30 minutes
concentrationconcentrated in vacuo
customwere precipitated from ethyl acetate with hexanes

Sources & evidence

ORD record: ord-23360a6e84044b40bc695d9efbff26b0
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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