Tetrabutylammonium Fluoride → HCID 16043212, compound

HRID 604460Notes

Reaction equation

[CH:1]([C:4]1[S:8][C:7]([N:9](COCC[Si](C)(C)C)[S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[S:25][C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)=[N:23][C:22]=3[CH3:36])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:6][N:5]=1)([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH:1]([C:4]1[S:8][C:7]([NH:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]3[S:25][C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=4)=[N:23][C:22]=3[CH3:36])=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

160 mg of N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-4-[4-methyl-2-(4-trifluoromethylphenyl)-thiazol-5-ylmethoxy]-N-(2-trimethylsilanyl-ethoxymethyl)-benzenesulfonamide were dissolved in 3.8 ml tetrahydrofuran. 977 mg tetra-N-butylammoniumfluoride were added and the reaction mixture was stirred at room temperature for two hours and at 40° C. for twenty minutes. The solvent was removed in vacuo and the residue purified by RP-HPLC to obtain 32 mg N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzenesulfonamide as amorphous solid.

Workup

customThe solvent was removed in vacuo
customthe residue purified by RP-HPLC

Sources & evidence

ORD record: ord-8777cc90f9384cd6a9f1302439d0ab1e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910612B2

Reaction notes

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