1-Hydroxybenzotriazole → (3aR,6aS)-tert-butyl 5-(5-(2-(trifluoromethyl)benzylcarbamoyl)pyridin-3-yl)hexahydropyrrolo [3,4-c]pyrrole-2(1H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-(Trifluoromethyl)benzylamine	HCID 76447	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	5-((3aR,6aS)-5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinic Acid	HCID 67265367	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Pyridine	HCID 1049	—
Product	(3aR,6aS)-tert-butyl 5-(5-(2-(trifluoromethyl)benzylcarbamoyl)pyridin-3-yl)hexahydropyrrolo [3,4-c]pyrrole-2(1H)-carboxylate	HCID 67265605	—

Reaction Conditions

Temperature	33 °C

Reaction Steps

A suspension of the product from Example 33B (52.5 mg, 0.16 mmol), 2-trifluoromethylbenzylamine (33.3 mg, 0.19 mmol), 1-hydroxybenzotriazole (30.1 mg, 0.20 mmol), 4-dimethylaminopyridine (4 mg, 0.03 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (34.3 mg, 0.24 mmol) in pyridine (7.0 mL) were stirred at 33° C. for 18 h. The reaction mixture was filtered through a glass microfiber frit and rinsed with methanol. The filtrate was concentrated and the residue was purified by silica gel chromatography (EtOAc, Rf=0.2) to afford the title compound. MS (APCI) m/z 491 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08648084B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-1a36cd94b3584c37af8644d1f0165c7c
Source note	uspto-grants-2014_02