(R)-2-(pyridin-2-yl)but-3-yn-2-ol → 9-((R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	(R)-2-(pyridin-2-yl)but-3-yn-2-ol	HCID 42554703	—
Reactant	Ethyl 9-bromo-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate	HCID 86693327	—
Reactant	4-Methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate	HCID 86693551	—
Product	9-((R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide	HCID 86693550	—

Reaction Steps

Similar to as described in General Procedure G, ethyl 9-bromo-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate was reacted with (R)-2-(pyridin-2-yl)but-3-yn-2-ol to give a diasteromeric mixture of ethyl 94(R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate. Following aminolysis of the ethyl ester (similar to as described in General Procedure M) a diasteromeric mixture of the titled compounds was obtained and separated by Prep HPLC.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034866B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-c2bc06b7ca064a1b8b2a68a514cf8a5b
Source note	uspto-grants-2015_05