4-Methylmorpholine → Ethyl 2-[(3R)-3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}pyrrolidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
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 2-[(3R)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate	HCID 68406312	—
Product	Ethyl 2-[(3R)-3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}pyrrolidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate	HCID 68406127	83.6%

Reaction Steps

The same operation as in Example (217c) was performed using ethyl 2-[(3R)-3-aminopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (238a) (116 mg, 0.45 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (79 mg, 0.45 mmol), WSC hydrochloride (260 mg, 1.36 mmol), 1-hydroxybenzotriazole (61 mg, 0.45 mmol) and N-methylmorpholine (0.10 mL, 0.90 mmol), to obtain 155 mg of the title compound as a white solid (83%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536197B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-f00988474d4e4525b510910ae6e91078
Source note	uspto-grants-2013_09