Hydrochloric Acid → HCID 178502308, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid	HCID 10942966	—
Reactant	(S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate	HCID 178451893	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 178502308	HCID 178502308	47.2%

Reaction Conditions

Temperature	0 °C

Reaction Steps

(S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.10 g, 2.64 mmol) was dissolved in DCM (15 mL) and HCl (4M in dioxane, 3 mL) was added. After stirring for 2.5 h, the reaction mixture was concentrated and the residue was treated with (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (462 mg, 2.64 mmol), HATU (1.003 g, 2.64 mmol) and DMF (13 mL). The stirred mixture was cooled to 0° C. and DIPEA (2.3 mL, 13.2 mmol) was added. After 7 min, the reaction was allowed to warm to RT. 20 min later, the mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (79% to 100% EtOAc/hexane) to afford the title compound (590 mg, 47%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09156823B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-2aa4b5d8be7c46beb8da1dd8c386385b
Source note	uspto-grants-2015_10