(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide formate

Participants

Role	Name	HCID	Charge
Reactant	(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide	HCID 46946413	—
Reactant	Lithium 1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carboxylate	HCID 86692763	—
Product	(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide formate	HCID 86692762	—

Reaction Steps

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carboxylate 20D carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide formate 1:1 epimers as a white solid (73%). MS ISP (m/e): 618.3 (100) [(M+H)]]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08802665B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-b0a1b3c8b41342d8ada71bd3d281a05e
Source note	uspto-grants-2014_08