1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl cis(+/-)-4-{[(4,5-dibromo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4,5-dibromo-1H-imidazole-2-carboxylic acid	HCID 12630333	—
Reactant	(3R,4S)-4-Amino-1-boc-3-methoxypiperidine	HCID 57362389	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Product	tert-Butyl cis(+/-)-4-{[(4,5-dibromo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate	HCID 86648455	72%

Reaction Steps

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1e) (300 mg, 1.30 mmol), 4,5-dibromoimidazole-2-carboxylic acid obtained in Example (2a) (300 mg, 1.11 mmol), WSC hydrochloride (460 mg, 2.40 mmol) and DMAP (50 mg, 0.41 mmol), to obtain 384 mg of the title compound as a white solid (72%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-ac335fe48ed745a38e5f9471bc526b10
Source note	uspto-grants-2015_01