1,4-Dioxane → HCID 86620098, compound

HRID 2243901Notes

Reaction equation

HRID 2243901 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[C:16]([S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[C:15]([C:31]#[N:32])=[N:14]1.C(N(C(C)C)CC)(C)C.O1CCOCC1.[CH3:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54].C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([N:18]2[CH2:19][CH2:20][N:21]([CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:22][CH2:23]2)=[C:16]([S:24]([C:27]([F:28])([F:30])[F:29])(=[O:26])=[O:25])[C:15]([C:31]#[N:32])=[N:14]1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 11569935HCID 11569935, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 86620098HCID 86620098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-piperazin-1-yl-4-[(trifluoromethyl)sulfonyl]-1H-pyrazole-3-carbonitrile (0.40 g, 0.8 mmol) and diisopropylethylamin (0.13 g, 1.0 mmol) in dioxane (5 mL) benzylbromide (0.14 g, 0.8 mmol) was added and refluxed for 5 h. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound 01-45, 0.31 g) as an oil; 1H-NMR: 2.30(4H), 3.19 (4H), 3.45 (2H), 7.25 (5H), 7.82 (2H); 19F-NMR: −64.1 (PhCF3); −79.6 ppm (SO2CF3).

Workup

  1. additionwas added
  2. temperaturerefluxed for 5 h

Sources & evidence

ORD record
ord-826329cf53ac4b2989f2593c8d981bba
Source dataset
uspto-grants-2010_03
Patent number
US07678797B2

Reaction notes

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