Hydrochloric Acid → N-(5,8-Dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidin 2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide

HRID 1391843Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[CH3:15][O:16][C:17]1[C:22]([S:23](Cl)(=[O:25])=[O:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=[CH:19][N:18]=1.N1C=C(C)C=C(C)C=1.Cl>C(#N)C.CS(C)=O>[CH3:14][O:13][C:5]1[N:4]2[N:3]=[C:2]([NH:1][S:23]([C:22]3[C:17]([O:16][CH3:15])=[N:18][CH:19]=[CH:20][C:21]=3[C:27]([F:30])([F:28])[F:29])(=[O:24])=[O:25])[N:10]=[C:9]2[C:8]([O:11][CH3:12])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (19.5 g, 0.10 mol) and 2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride (27.5 g, 0.10 mol) were combined in acetonitrile (35 mL). To this was added 3,5-lutidine (32 g, 0.30 mol), followed by DMSO (0.23 g, 0.0030 mol). A slight exotherm was noted (to about 30° C.) in the initial hours as the reaction slurry was stirred at ambient conditions for 17 hours. The mixture was then warmed to 40° C. and treated with 2 N HCl (140 mL). The new slurry was stirred while being allowed to cool to room temperature over one hour. The solids were isolated by filtration, washed with water, and dried under vacuum to afford 38 g of product as a solid assaying at 97 wt % (85% yield).

Workup

custom(to about 30° C.)
stirringThe new slurry was stirred
temperatureto cool to room temperature over one hour
customThe solids were isolated by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-c1293ec1e7b743d8828d074bf2e05839
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07339058B2

Reaction notes

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