1-Hydroxybenzotriazole → Ethyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylbenzoate

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid	HCID 67548929	—
Reactant	Ethyl 3-[(3R,4S)-4-amino-3-methoxypiperidin-1-yl]-5-methylbenzoate	HCID 86648852	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	Ethyl cis(+/-)-3-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylbenzoate	HCID 86648854	76.4%

Reaction Steps

The same operation as in Example (1g) was performed using ethyl cis(±)-3-(4-amino-3-methoxypiperidin-1-yl)-5-methylbenzoate obtained in Example (259g) (about 0.24 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (37 mg, 0.21 mmol), WSC hydrochloride (134 mg, 0.70 mmol), HOBT (47 mg, 0.35 mmol), dichloromethane (1.5 mL) and DMA (1.5 mL), to obtain 72 mg of the title compound as a colorless oily substance (75%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-3035f0980ec94478b0fe2bdf9802c7d5
Source note	uspto-grants-2015_01