Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,2-Dihydro-2,7-naphthyridin-1-one	HCID 820151	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate	HCID 86700141	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate	HCID 86700191	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (36.7 mg, 0.076 mmol) and 2,7-naphthyridin-1(2H)-one (14.0 mg, 0.092 mmol) in DMF (0.9 mL) was added CuI (9.0 mg, 0.046 mmol) and trans-N1,N2-dimethylcyclohexane-1,2-diamine (15 μL, 0.092 mmol) and K2CO3 (21.0 mg, 0.152 mmol). The reaction was heated at 110° C. for 2 h. After cooling, the reaction mixture was diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C30H29ClN3O4S: 562.2; found: 562.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987250B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-555d933074ff4c19a9a4e5636c43f1f1
Source note	uspto-grants-2015_03