2,4-DIFLUOROBENZENESULFONAMIDE

Step 4: Preparation of 2-fluoro-4-hydrazinobenzenesulfonamide General procedure: Intermedite 16 (0.69mmol, 1 equiv.), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.26g, 1.38mmol, 2 equiv.), 4-dimethylaminopyridineand (DMAP) (0.17g, 1.38mmol, 2 equiv.) and different appropriate sulfanilamides (1.5 equiv.) were dissolved in DMF (10mL). The reaction mixture was stirred at ambient temperature for 12h and then evaporated under reduced pressure. Water (30mL) was added and extracted with EA (3×10mL). Combined organic phase was washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified on silica gel using EA-PE system and pure fractions were collected, concentrated and recrystallized, giving the desired compounds (41-48).12.28 g (63.6 mmol) of 250ml 2, 4 round bottom flask benzenesulfonyl chloride there was obtained: (2, 4-difluorobenzenesulfonyl chloride) (2g, 10mmol) and 2, 4-difluoro-benzenesulfonamide (Step 1: (S) -tert-Butyl (1- (2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) -4- ( ( (2, 4-difluorophenyl) sulfonyl) carbamoyl) oxazol-5-yl) ethyl) carbamate[0962]To 10 mL of anhydrous tetrahydrofuran were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (0.3 g, 0.64 mmol) and 1, 1' -carbonyldiimidazole (312 mg, 1.92 mmol) . The mixture was stirred at 60 for 30 minutes. The reaction mixture was cooled to rt, degassed and refilled with nitrogen, then a solution of 2, 4-difluorobenzenesulfonamide (247 mg, 1.28 mmol) and 1, 8-diazabicyclo [5.4.0] undec-7-ene (0.14 mL, 0.96 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise. After addition, the mixture was stirred at 60 for 12 hours. To the reaction mixture was added saturated aqueous ammonium chloride (15 mL) . The resulting mixture was extracted with ethyl acetate (15 mL × 3) . The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) 20/1) to give the title compound as a yellow solid (0.4 g, 99) .[0963]1H NMR (400 MHz, CDCl3) : delta (ppm) 8.26 -8.22 (m, 1H) , 7.59 -7.54 (m, 2H) , 7.27 -7.26 (m, 1H) , 7.14 -7.10 (m, 1H) , 7.02 -6.97 (m, 1H) , 6.75 (t, JF-H 74.9 Hz, 1H) , 5.28 -5.25 (m, 1H) , 4.04 (d, J 6.9 Hz, 2H) , 1.50 (d, J 7.1 Hz, 3H) , 1.39 (s, 9H) , 1.34 -1.33 (m, 1H) , 0.74 -0.72 (m, 2H) , 0.49 -0.45 (m, 2H) .[00397] A mixture of 6-chloro-8-iodo[1, 2, 4]triazolo[1, 5-a]pyridine (0.3 15 g, 1.13 mmol), 2, 4- difluorobenzenesulfonamide (0.258 g, 1.34 mmol), copper(I) iodide (32 mg, 0.17 mmol) and cesium carbonate (0.776 g, 2.38 mmol) were placed in a microwave vial. The vessel was evaculated and backfilled with argon 3 times. DMF (4.73 niL) and ethylenediamine (82 mg, 1.4 mmol) were added. The mixture was subjected to microwave irradiation at 120 C for 30 mm. The reaction mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to give N-(6- chloro[1, 2, 4]triazolo[1, 5-a]pyridin-8-yl)-Step 3: N-(6-chloro[1, 2, 4]triazolo[1, 5-a]pyridin-8-yl)-

Molecular Weight:193.17
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:193.00090590
Monoisotopic Mass:193.00090590
Topological Polar Surface Area:68.5
Heavy Atom Count:12
Complexity:249
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes