Pyridine → Methanesulfonamide, N-(3-((4R)-4-(3,3-dimethylbutyl)-3,4-dihydro-1-hydroxy-4-methyl-3-oxo-2-naphthalenyl)-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl)-

Participants

Role	Name	HCID	Charge
Reactant	Pyridine	HCID 1049	—
Reactant	Methanesulfonyl chloride	HCID 31297	—
Reactant	(1R)-3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1-(3,3-dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1H)-one	HCID 135869465	—
Solvent	Dichloromethane	HCID 6344	—
Product	Methanesulfonamide, N-(3-((4R)-4-(3,3-dimethylbutyl)-3,4-dihydro-1-hydroxy-4-methyl-3-oxo-2-naphthalenyl)-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl)-	HCID 135430231	87.2%

Reaction Steps

To a solution of the product of Example 49-6 (235.0 g, 0.518 mol) and pyridine (123.0 g, 1.55 mol) in dichloromethane (1645 mL) at 18-20° C. was added methane sulfonyl chloride (89.0 g, 0.777 mol) over 45 minutes. The solution was mixed at RT for 3.5 h then quenched with 1 M HCl (1500 mL). The layers were separated and the organic layer was concentrated under vacuum. The product was crystallized from ethyl acetate/heptane (1/1, 8 volumes) to give the title compound (240.01 g, 87%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07538105B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-d948df74791f4d48a6eb68fe6b465990
Source note	uspto-grants-2009_05