Hydrochloric Acid → 5,7-dimethyl-N-(2,6-difluorophenyl)pyrazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1493535Notes

Reaction equation

C([C:6]1[C:7]([S:17]([NH:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])(=[O:19])=[O:18])=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)(OCC)=O.Cl.O>CC(O)=O>[CH3:16][C:12]1[CH:13]=[C:14]([CH3:15])[N:9]2[N:8]=[C:7]([S:17]([NH:20][C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])(=[O:18])=[O:19])[CH:6]=[C:10]2[N:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A slurry of 4.8 g (10.8 mmole) of 3-carboethoxy-5,7-dimethyl-N-(2,6-difluorophenyl) pyrazolo-[1,5-a]pyrimidine-2-sulfonamide in 30 ml glacial HOAc was stirred at room temperature with 1 ml concentrated HCl and 3 ml water for 2 hours. The mixture was then heated at 110° C. for 16 hours. A further 1 ml concentrated HCl and 5 ml water were added and the mixture stirred for 16 hours, then cooled to room temperature. The mixture was thrown onto ice and the resultant solid collected by filtration, washed with water and dried to give 2.34 g (64 percent) of the product as a brown powder, m.p. 201°-208° C. An analytical sample was recrystallized from CH3CN/EtOAc/-CH3OH, m.p. 209°-211° C. (dec). 1H NMR (DMSO-d-6): 10.3 (s, 1H, NH), 7.37 (m, 1H, benzene), 7.10 (m including s, 3H, aromatic and H-3 or H-6), 6.82 (s, 1H, H-3 or H-6), 2.63 (s, 3H, CH3), 2.53 (s, 3H, CH3) IR (KBr): 3400, 3050, 2800, 1625, 1600, 1540, 1480, 1430, 1325, 1290, 1240, 1170, 1140, 1000.

Workup

temperaturecooled to room temperature
filtrationthe resultant solid collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-c53dd5da24254d0f9603cce8d6178fe6
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021591

Reaction notes

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