Potassium Carbonate → HCID 66652799, compound

HRID 509107Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17]>CS(C)=O>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:17]

Participants

Conditions

Temperature: 50 °C

Procedure

3-Methoxythiophenol (0.0801 g, 0.571 mmol) and potassium carbonate (0.158 g, 1.14 mmol) were stirred in dimethylsulphoxide. 3-Cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.248 g, 0.571 mmol) was added to the reaction mixture and the mixture stirred at 50° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. A 1M aqueous solution of sodium hydroxide was added to the mixture. The organic layer was separated and dried over MgSO4, filtered and concentrated in vacuo to afford a white solid. The solid was triturated in ethyl acetate and filtered to afford the title compound (0.204 g, 64%).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
additionA 1M aqueous solution of sodium hydroxide was added to the mixture
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford a white solid
customThe solid was triturated in ethyl acetate
filtrationfiltered

Sources & evidence

ORD record: ord-e46da6020f204724a06a940a2affd10e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096558B2

Reaction notes

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