Water → HCID 86721281, compound

HRID 1750439Notes

Reaction equation

[H-].[Na+].[C:3]([N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:10]([C:20]2[S:21][CH:22]=[C:23]([CH:25]=O)[N:24]=2)[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4].[OH2:27].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[C:3]([N:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[C:10]([C:20]2[S:21][CH:22]=[C:23](/[CH:25]=[CH:29]/[C:30]([O:31][CH2:32][CH3:28])=[O:27])[N:24]=2)[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4]

Participants

Reactant 4

HCID 962Water

HCID 8028Tetrahydrofuran2×

HCID 24758Sodium hydride

HCID 86721280HCID 86721280, compound

Product 1

HCID 86721281HCID 86721281, compoundYield 25.3%

Procedure

To a solution of triethyl phosphonoacetate (0.026 ml, 0.13 mmol) in THF (2.0 mL) was added sodium hydride (55 wt % paraffin oil, 5.15 mg, 0.13 mmol) at 0° C., and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added a solution of the compound (40 mg, 0.12 mmol) obtained in step 3 in THF (2.0 mL) at 0° C., and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure, and the residue was crystallized from diethyl ether-hexane to give ethyl(E)-3-(2-(1-(tert-butyl)-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acrylate (12.2 mg, 0.030 mmol, 25.3%) as a white powder.

Workup

stirringthe mixture was stirred at room temperature for 5 hr
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
customdried
customthe solvent was evaporated under reduced pressure
customthe residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record: ord-7b8361b420df49db815815ba925b1bb6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156837B2

Reaction notes

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