Morpholine → N-cyclopropylsulfonyl-13-methyl-17-(2-morpholin-4-ylpyrimidin-4-yl)oxy-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide	HCID 72253694	—
Solvent	1,2-Dichloroethane	HCID 11	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-cyclopropylsulfonyl-13-methyl-17-(2-morpholin-4-ylpyrimidin-4-yl)oxy-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide	HCID 75277256	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

Compound 10f (31 mg, 0.052 mmol) and morpholine (0.1 ml) in THF was left at ambient temperature for 20 hrs, volatiles were stripped of and the residue was dissolved in DCE (15 ml) to which Hoyeda-Grubbs II catalyst (7 mg) was added. The mixture was heated in a microwave oven at 150° C. for 10 min under an atmosphere of nitrogen, then concentrated to dryness and purified by column chromatography on silica gel eluted with DCM-MeOH 2% followed by prep. HPLC-MS-UV to give pure title compound, (4.7 mg), (M+H)+616.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08937080B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-260d242a672143c88b65a3f3221c55c0
Source note	uspto-grants-2015_01