Dimethylamine, hydrochloride → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(dimethylcarbamoyl)-1,3-thiazole-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine, hydrochloride	HCID 10473	—
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-methoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid	HCID 86648511	—
Product	Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(dimethylcarbamoyl)-1,3-thiazole-5-carboxylate	HCID 86648532	77%

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-methoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid obtained by the method described in Example (50a) (65 mg, 0.13 mmol), dimethylamine hydrochloride (29 mg, 0.36 mmol), WSC hydrochloride (78 mg, 0.41 mmol) and HOBT (20 mg, 0.15 mmol), to obtain 52.9 mg of the title compound (77%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-b1c720448ae8418dbb798e3a1ef1f8eb
Source note	uspto-grants-2015_01