Water → 9-[4-(Cyclohexyloxy)phenyl]-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Ethanesulfonylchloride, 2-chloro-	HCID 15385	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	3-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amine	HCID 66748148	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	9-[4-(Cyclohexyloxy)phenyl]-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide	HCID 66748512	83.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 3-[4-(cyclohexyloxy)phenyl]pyrazin-2-amine (470 mg) in THF (dry) (25.00 mL) was added to a mixture of NaH (60%, 349 mg) and 2-chloroethanesulfonyl chloride (853 mg) in THF (dry) (25 mL) at room temperature. The mixture was stirred at room temperature overnight and 80° C. for 3 hr. Water was added and THF was removed in vacuo. A precipitate was collected by filtration and washed with water-Et2O to give the title compound (522 mg) as a yellow solid. The solid was crystallized from CH3CN-IPE to give a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08778934B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-8bb74f88550644e0a6872fb339a941c1
Source note	uspto-grants-2014_07