Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-[2-(1-Carbamoylethylcarbamoyl)quinolin-6-yl]-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-	HCID 18462	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	L-Alaninamide	HCID 444939	—
Reactant	PyBroP	HCID 2733179	—
Reactant	6-(1-Cyclohexyl-5-ethoxycarbonyl-1H-benzimidazol-2-yl)quinoline-2-carboxylic Acid	HCID 57602995	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-[2-(1-Carbamoylethylcarbamoyl)quinolin-6-yl]-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl Ester	HCID 68919557	42.3%

Reaction Steps

A solution of 100 mg (0.23 mmol) of Compound 402a, 86 mg (0.69 mmol) of L-alaninamide, 322 mg (0.69 mmol) of PyBroP, 84 mg (0.69 mmol) DMAP and 89 mg (0.69 mmol) DIEA in 5 mL anhydrous CH2Cl2 was stirred at room temperature for 24 h. To this solution was added 214 mg (0.92 mmol) of CSA. The solution was stirred for another 24 h, diluted with 10 mL CH2Cl2 and washed with 10 mL H2O. The solvent was dried and evaporated. The residue was chromatographed on silica gel using first hexane/EtOAc then CH2Cl2/MeOH as eluent yielding 50 mg yellow oil. MS: 514.28 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07511145B2
Source dataset	uspto-grants-2009_03
ORD ID	ord-ef9a621588f5428ca617a34cf18decac
Source note	uspto-grants-2009_03