6-Chloropyridine-3-sulfonamide

6-Chloro-pyridine-3-sulfonyl chloride (5.Og, 0.024mol) was dissolved in a 0.5M solution of ammonia in dioxane (125mL) at -56-Chloro-pyridine-3-sulfonic acid amide; 6-Chloro-pyridine-3-sulfonyl chloride (5.Og, 0.024mol) was dissolved in a 0.5M solution of ammonia in dioxane (125mL) at -5°C. The mixture was allowed to warm to room temperature and the mixture stirred for 1 hour. The mixture was filtered through celite, washed twice with dioxane and concentrated in vacuo to afford -choro-pyridine-S-sulfonic acid amide as an off white solid 4.55g (98percent yield). LC (at)UV215nm; Rt 1.05: 100percent, m/z (ES+): 193/195 (400 MHz; d6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with Hβ-chloropyridine-S-sulfonamide. 6-chloropyridine-3-sulfbnyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 niL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with H6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with HA solution of 6-chloropyridine-3-sulfonyl chloride (50 g) in MeCN (75 ml) was added dropwise to aq NH4OH (28-30%, 125 ml) at 0 C. (ice bath) (exthothermic). After addition, the ice bath was removed and the reaction mixture was stirred for another 45 min, and then cooled down to 0 C. again, quenched with water and acidified with 37% HCl (120 ml) to pH 1-2. The mixture was extracted with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product (40 g) was dried overnight under high vacuum and used directly for the next step. The crude product, Under N2 and to a 250 mL RBF, was added Step 1. A mixture of To a suspension of 6-chloropyridine-3 -sulfonamide in ethanol (0.3 M) in a microwave compatible vessel was added (4-(trifluoromethyl)phenyl)methylamine. The reaction mixture was heated at 150 C in Biotage Initiator for 1 hour. The reaction mixture was quenched by addition of H20, extracted with EtOAc, dried over MgS04, filtered and concentrated in vacuo to give the title compound as an off-white solid.

Molecular Weight:192.62
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:191.9760263
Monoisotopic Mass:191.9760263
Topological Polar Surface Area:81.4
Heavy Atom Count:11
Complexity:223
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes