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

HRID 509100
Notes
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Reaction equation

HRID 509100 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666527743-Cyano-N-(2,4-dimethoxybenzyl)-4-[2-pyridazin-4-yl-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 565980593-Cyano-4-[2-pyridazin-4-yl-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. temperaturewarming slowly to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue re-dissolved in methanol
  4. customOnce again the solvent was removed in vacuo
  5. filtrationfiltered through Celite™
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes