Triethylamine → tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	rac-tert-butyl (3R,4R)-4-amino-3-fluoropiperidine-1-carboxylate	HCID 45489895	—
Reactant	4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid	HCID 67548929	—
Product	tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidine-1-carboxylate	HCID 86648769	72.1%

Reaction Steps

The same operation as in Example (196d) was performed using tert-butyl trans(±)-4-amino-3-fluoropiperidine-1-carboxylate obtained in Example (197a) (30.0 mg, 0.137 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (28.8 mg, 0.165 mmol), 1-hydroxybenzotriazole hydrate (27.9 mg, 0.206 mmol), WSC hydrochloride (39.5 mg, 0.206 mmol) and triethylamine (28.7 μL, 0.206 mmol), to obtain 37.0 mg of the title compound (72%) as a pale yellow foamy substance.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-cebe27463fc94a899d739cd51881a829
Source note	uspto-grants-2015_01