Water → HCID 68778588, compound

HRID 2263153Notes

Reaction equation

[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[OH-:29].[Na+].O>CO.O1CCCC1>[NH2:2][C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[S:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:19]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:5][CH:4]=1)=[O:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(6-cyanopyridin-3-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide (100 mg, 0.255 mmol) in methanol/tetrahydrofuran (1:4) (15 ml) was added a 1N aqueous sodium hydroxide solution (2.56 ml, 2.55 mmol) at room temperature, and the mixture was stirred at 60° C. for 2 days. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 12.8 mg (12.2%) of the desired product as a solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-d7dccbffd1a14dd88ac84cecf97bcb93
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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