Trifluoroacetic acid → 1-(2-Bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-YL)isoquinoline-6-sulfonamide
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3)[C:26]3[S:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([NH:25][C:26]3[S:30][N:29]=[CH:28][N:27]=3)(=[O:23])=[O:24])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (INTERMEDIATE DD, 100 mg, 0.157 mmol) in DCM (1574 μl) was added TFA (60.6 μl, 0.787 mmol). The mixture was stirred at room temperature. After 2 h, LC/MS showed mainly the desired product. The reaction mixture was concentrated and dissolved in 3 ml of DMSO. This solution was injected onto the reverse phase HPLC (Xbridge 10 μm, C18, 19×100 mm column eluting with 0.1% NH4OH in ACN and water as the mobile phase) ultimately affording 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (10.6 mg, 0.021 mmol). MS (ESI): 514.8 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ ppm 7.68 (d, J=8.87 Hz, 1H), 7.76 (d, J=7.80 Hz, 1H), 7.90-7.98 (m, 2H), 8.22-8.26 (m, 2H), 8.48 (s, 1H), 8.65 (m, 1H), 8.76 (d, J=5.66 Hz, 1H).
Sources & evidence
- ORD record
- ord-cebc0a4577a54e91bdc508915e0f5220
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
Loading…