2-Methoxyethylamine → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(methoxyethyl)carbamoyl]-1,3-thiazole-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Methoxyethylamine	HCID 8018	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid	HCID 86648529	—
Product	Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(methoxyethyl)carbamoyl]-1,3-thiazole-5-carboxylate	HCID 131730858	72.5%

Reaction Steps

The same operation as in Example (1g) was performed using cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid obtained in Example (68c) (112 mg, 0.22 mmol), methoxyethylamine (40 μL, 0.46 mmol), WSC hydrochloride (130 mg, 0.68 mmol) and HOBT (30 mg, 0.22 mmol), to obtain 88.8 mg of the title compound as a white solid (71%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536197B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-386145f2b84644ed858d9b12661bb3e1
Source note	uspto-grants-2013_09