Isopropylamine → N-cyclopropylsulfonyl-13-methyl-2,14-dioxo-17-[2-(propan-2-ylamino)pyrimidin-4-yl]oxy-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Isopropylamine	HCID 6363	—
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-2,14-dioxo-17-[2-(propan-2-ylamino)pyrimidin-4-yl]oxy-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide	HCID 75277257	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

Compound 10f (30 mg, 0.05 mmol) and isopropylamine (excess) in THF (10 ml) was heated in a microwave oven at 110° C. for 30 min and then left at ambient temperature for 16 hrs. The solvent was stripped of and the residue was redissolved in DCE (15 ml) and degassed with nitrogen. Hoyeda-Grubbs II catalyst (7 mg) was added and the mixture was heated in a microwave oven at 150° C. for 10 min. The mixture was concentrated to dryness and purified by prep. HPLC-MS-UV which gave the pure title compound (3.1 mg), (M+H)+=589.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08937080B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-4de7c34782bd476aa8aed69a69286c35
Source note	uspto-grants-2015_01