Trifluoroacetic acid → 3-Cyano-4-[2-pyridazin-4-yl-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 509100Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([S:26]([N:29](CC2C=CC(OC)=CC=2OC)[C:30]2[S:34][N:33]=[CH:32][N:31]=2)(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[C:20]1[CH:25]=[CH:24][N:23]=[N:22][CH:21]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:26]([NH:29][C:30]2[S:34][N:33]=[CH:32][N:31]=2)(=[O:27])=[O:28])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[CH:12][C:11]=1[C:20]1[CH:25]=[CH:24][N:23]=[N:22][CH:21]=1)#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Cyano-N-(2,4-dimethoxybenzyl)-4-[2-pyridazin-4-yl-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 34, 54 mg, 0.083 mmol) was dissolved in dichloromethane (0.75 mL) and cooled to 0° C. Trifluoroacetic acid (32 μL, 0.41 mmol) was added as a solution in dichloromethane (0.25 mL) and the reaction stirred for 2 hours warming slowly to room temperature. The solvent was removed in vacuo and the residue re-dissolved in methanol. Once again the solvent was removed in vacuo. The material was suspended in methanol and filtered through Celite™. The reaction mixture was concentrated in vacuo and purified by the basic preparative HPLC method to afford the title compound.

Workup

temperaturewarming slowly to room temperature
customThe solvent was removed in vacuo
dissolutionthe residue re-dissolved in methanol
customOnce again the solvent was removed in vacuo
filtrationfiltered through Celite™
concentrationThe reaction mixture was concentrated in vacuo
custompurified by the basic preparative HPLC method

Sources & evidence

ORD record: ord-904c9d206457447dba1be36f654282d4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096558B2

Reaction notes

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