Cesium carbonate → HCID 86685990, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,2-Diaminocyclohexane, (+)-	HCID 479307	—
Reactant	6-Chloro-3,4-dihydroisoquinolin-1(2H)-one	HCID 19375637	—
Reactant	HCID 80202111	HCID 80202111	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 86685990	HCID 86685990	26%

Reaction Steps

6-Chloro-3,4-dihydro-2H-isoquinolin-1-one (intermediate A-2) (36 mg, 0.2 mmol), [1-(5-bromo-pyridin-3-yl)-ethyl]-methyl-amine (85.6 mg, 0.4 mmol), CuI (3.8 mg, 0.02 mmol), (1S,2S)-cyclohexane-1,2-diamine (4.5 mg, 0.04 mmol) and Cs2CO3 (130 mg, 0.4 mmol) were dissolved in 1,4-dioxane (5 mL). The reaction mixture was subject to microwave reaction at 150° C. for 2.5 hours before it was poured into H2O (15 mL) and extracted with EtOAc (2×10 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to yield the title compound (15 mg, 26%) as a white solid. MS: 316.2 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133158B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-1b461168ca6145babb84c386cf430c38
Source note	uspto-grants-2015_09