Hydrochloric Acid → HCID 178502472, 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	HCID 178452509	HCID 178452509	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 178502472	HCID 178502472	54.3%

Reaction Steps

(1R,3S,4S)-tert-butyl 3-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (200 mg, 0.45 mmol) in DCM (5 mL) was added HCl (4M in dioxane, 1 mL). The solution stirred for 1 h, after which the solvent was removed. The intermediate (154 mg, 0.45 mmol) was dissolved in DMF (5 mL). (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (79 mg, 0.45 mmol), HATU (171 mg, 0.45 mmol), and DIPEA (0.39 mL, 2.25 mmol) were added sequentially. After stirring o/n, the solution was diluted with EtOAc, washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The mixture was purified by silica gel chromatography to yield product (122 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09156823B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-7bd5e9081c9f45acada43dccb2f20bc0
Source note	uspto-grants-2015_10