Acetoxyacetic acid → N-((6-(7-(6-(3-cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-hydroxy-N-(2-methoxyethyl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Acetoxyacetic acid	HCID 83766	—
Reactant	tert-butyl 4-(2-(4-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate	HCID 67440535	—
Reactant	2-(((6-(7-(6-(3-Cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)(2-methoxyethyl)amino)-2-oxoethyl acetate	HCID 67442179	—
Reactant	1-Cyclopropyl-3-(3-fluoro-4-(2-(5-(piperazin-1-ylmethyl)pyridin-2-yl)thieno[3,2-b]-pyridin-7-yloxy)phenyl)urea	HCID 67442388	—
Product	N-((6-(7-(6-(3-cyclopropylureido)pyridin-3-yloxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-hydroxy-N-(2-methoxyethyl)acetamide	HCID 67442923	—

Reaction Steps

Compounds 309 (example 167) and 310 (example 168) were prepared by reacting compounds 307 (scheme 68) and compound 49 (scheme 15) with acetoxyacetic acid, similarly to compound 30 (scheme 13). Compound 311 (example 169) was synthesized by following the procedures described above for the synthesis of compound 49 (scheme 15). Compounds 312 (example 170) and 313 (example 171) were obtained similarly to compound 31 (scheme 13). Compound 314 (example 172) was synthesized by following the procedures described above for the synthesis of compound 75 (scheme 20).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906852B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-d839a54d74cb4d2889266850b5236450
Source note	uspto-grants-2014_12