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

Participants

Role	Name	HCID	Charge
Reactant	N-(2-aminoethyl)acetamide	HCID 66082	—
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(+/-)-4-[(2-acetamidoethyl)carbamoyl]-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate	HCID 86648841	57.4%

Reaction Steps

The same operation as in Example (247a) 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 (50a) (200 mg, 0.40 mmol), N-acetylethylenediamine (0.08 mL, 0.80 mmol), WSC hydrochloride (230 mg, 1.20 mmol) and 1-hydroxybenzotriazole (54 mg, 0.40 mmol), to obtain 134 mg of the title compound as a white solid (57%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-b396207ff9d645889dacd7ee0349a45b
Source note	uspto-grants-2015_01