Diisopropylethylamine → HCID 53247239, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid	HCID 67259092	—
Reactant	HCID 67262013	HCID 67262013	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 53247239	HCID 53247239	—

Reaction Steps

The title compound is prepared analogously as described for example 28 using 1-{[1-(methoxymethyl)-1H-tetrazol-5-yl]methyl}-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (compound B48) (235 mg), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (165 mg; compound C10), TOTU (177 mg), HOAT (85 mg) and DIPEA (214 mg) in DCM (8 ml). After stirring for 4.5 h at RT additional 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (82.5 mg; compound C10), TOTU (177 mg) and HOAT (85 mg) are added. Purification by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)] gives the title compound as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09018175B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-d4ff55caf7154a7ab92375b31528e761
Source note	uspto-grants-2015_04