4-Methylmorpholine → Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-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-(3-aminoazetidin-1-yl)-1,3-benzothiazole-7-carboxylate	HCID 67549305	—
Product	Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-carboxylate	HCID 67548592	85.4%

Reaction Steps

The same operation as in Example (217c) was performed using ethyl 2-(3-aminoazetidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (224b) (273 mg, 0.98 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (166 mg, 0.95 mmol), WSC hydrochloride (547 mg, 2.85 mmol), 1-hydroxybenzotriazole (128 mg, 0.95 mmol) and N-methylmorpholine (0.21 mL, 1.90 mmol), to obtain 352 mg of the title compound as a pale yellow solid (85%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536197B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-abdbc2532f2a455d9df36509f3a54a18
Source note	uspto-grants-2013_09