Tetrahydrofuran → HCID 86620375, compound

HRID 1172161Notes

Reaction equation

HRID 1172161 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]([CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[CH3:19])=[C:16]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:15]([C:32]#[N:33])=[N:14]1.C(N(C(C)C)CC)(C)C.C1C[O:46][CH2:45]C1.CCCCCCC.C(OCC)(=O)C>O>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]([CH3:19])[CH2:20][CH:21]2[CH2:22][O:23][C:45](=[O:46])[O:24]2)=[C:16]([S:25]([C:28]([F:31])([F:29])[F:30])(=[O:26])=[O:27])[C:15]([C:32]#[N:33])=[N:14]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 16727055HCID 16727055, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 86620375HCID 86620375, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2,3-dihydroxypropyl)(methyl)amino]-4-[(trifluoromethyl)sulfonyl]-1H-pyrazole-3-carbonitrile (0.20 g, 0.4 mmol) and diisopropylethylamin (0.14 g, 1.1 mmol) in THF (10 mL) phosgene-toluene solution (0.22 g, 20% COCl2, 0.4 mmol) was added. The mixture was stirred at 20-30° C. for 20 h. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound 05-18, 0.14 g) as an oil; 1H-NMR: 2.88 (NMe), 3.35 and 3.45 (NCH2), 3.96 and 4.55 (CH2O), 4.82 (CHO), 7.87 (ArH) ppm; 19F-NMR: −63.8 (PhCF3); -78.8 ppm (SO2CF3).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-a36abcf0d6e7478ebbe8a49fbb20f09e
Source dataset
uspto-grants-2010_11
Patent number
US07834003B2

Reaction notes

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