3-cyano-4-[2-(5-methyl-1-trityl-1H-pyrazol-4-yl)-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide → 3-cyano-4-[2-(5-methyl-1H-pyrazol-4-yl)-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46246Notes

Reaction equation

HRID 46246 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:45]([NH:48][C:49]2[S:53][N:52]=[CH:51][N:50]=2)(=[O:47])=[O:46])[CH:6]=[CH:7][C:8]=1[O: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:21]=[N:22][N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:24]=1[CH3:25])#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([S:45]([NH:48][C:49]2[S:53][N:52]=[CH:51][N:50]=2)(=[O:47])=[O:46])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][C:11]=1[C:20]1[CH:21]=[N:22][NH:23][C:24]=1[CH3:25])#[N:2]

Participants

4

Reactant 1

HCID 594365913-cyano-4-[2-(5-methyl-1-trityl-1H-pyrazol-4-yl)-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 574948223-cyano-4-[2-(5-methyl-1H-pyrazol-4-yl)-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-cyano-4-[2-(5-methyl-1-trityl-1H-pyrazol-4-yl)-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 428, 345 mg, 0.46 mmol) was dissolved in 4N HCl in 1,4-dioxane (5 ml) and stirred at room temperature for 3 hours before concentrating in vacuo. The residue obtained was purified using an ISCO™ (12 g SiO2) eluting with methanol:dichloromethane (gradient 0:1 to 1:9, by volume). The purified compound was triturated with dichloromethane (10 mL) to afford the title compound as a white solid (148 mg, 34%-isolated as the hydrochloride salt).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue obtained
  3. customwas purified
  4. washeluting with methanol
  5. customThe purified compound was triturated with dichloromethane (10 mL)

Sources & evidence

ORD record
ord-5307fa7c26694b3fb0ad94944aecebb7
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

Loading…