Dimethylamine → HCID 10060670, compound

HRID 1063099Notes

Reaction equation

[C:1]([C:3]1[C:4]([S:17][CH2:18][C:19]([NH2:21])=[O:20])=[N:5][C:6](S(C(F)(F)F)(=O)=O)=[CH:7][C:8]=1[CH3:9])#[N:2].C(OC)(=O)C#CC.[CH3:29][NH:30][CH3:31].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>O1CCOCC1>[NH2:2][C:1]1[C:3]2[C:4](=[N:5][C:6]([N:30]([CH3:31])[CH3:29])=[CH:7][C:8]=2[CH3:9])[S:17][C:18]=1[C:19]([NH2:21])=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3-Cyano-4-methyl-6-trifluoromethanesulfonylpyridin-2-ylmercapto)acetamide (30.0 mg, 0.08 mmol) (prepared as described in Example 1 for the n-propyl analog but using methyl 2-butynoate) and dimethylamine (170.0 microL, 0.34 mmol) were mixed in 1,4-dioxane (0.5 mL) in a pressure tube and heated at 80° C. for 1 h. 2.0 M Aqueous sodium carbonate (520 μL, 1.04 mmol) was added, and the reaction heated at 100° C. for 6 h, then cooled to room temperature overnight. The mixture was poured into saturated aqueous ammonium chloride, and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 23.0 mg of the crude product. This was purified via automated flash silica chromatography (4 g silica gel column, 30-100% EtOAc/hexanes) to afford 9.0 mg (0.02 mmol, 45% yield) of the title compound.

Workup

temperaturethe reaction heated at 100° C. for 6 h
temperaturecooled to room temperature overnight
extractionextracted with EtOAc
extractionThe organic extract
washwas washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto afford 23.0 mg of the crude product
customThis was purified via automated flash silica chromatography (4 g silica gel column, 30-100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-afbaf8c557934cf7b897ffad2f1832ae
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964956B2

Reaction notes

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