Sodium Hydroxide → HCID 136052365, compound

HRID 1889486Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[C:17](=[O:18])[C:16]3[CH:19]=[C:20]([CH2:22][CH3:23])[S:21][C:15]=3[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]4[NH:41][C:40](=[O:42])[O:39][N:38]=4)=[CH:27][CH:26]=3)[C:13]2=[O:43])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[C:17](=[O:18])[C:16]3[CH:19]=[C:20]([CH2:22][CH3:23])[S:21][C:15]=3[N:14]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]4[NH:41][C:40](=[O:42])[O:39][N:38]=4)=[CH:29][CH:30]=3)[C:13]2=[O:43])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 5-chloro-2-[6-ethyl-2,4-dioxo-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl]benzoate (0.2 g), 1N aqueous sodium hydroxide solution (10 mL) and tetrahydrofuran (10 mL) was stirred at 100° C. for 2 hr. Tetrahydrofuran was evaporated under reduced pressure, and the residue was adjusted to pH 5 with chloroform and 1N hydrochloric acid, and extracted with chloroform. The obtained chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.13 g, 65%).

Workup

customTetrahydrofuran was evaporated under reduced pressure
extractionextracted with chloroform
washThe obtained chloroform layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-229270a6145041108b8b79ade4ac7155
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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