1-Hydroxybenzotriazole → Ethyl 2-((3R,4S)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-methoxy-1-methylethyl)carbamoyl]-1,3-thiazole-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Methoxyisopropylamine	HCID 123458	—
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 2-((3R,4S)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-methoxy-1-methylethyl)carbamoyl]-1,3-thiazole-5-carboxylate	HCID 68406005	80%

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) (250 mg, 0.50 mmol), 1-methoxy-2-propylamine (0.11 mL, 1.00 mmol), WSC hydrochloride (288 mg, 1.50 mmol) and 1-hydroxybenzotriazole (68 mg, 0.50 mmol), to obtain 228 mg of the title compound as a white solid (80%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-35298f05a5564bdd9dd155abadee50da
Source note	uspto-grants-2015_01