Ethanol heptane → (R)-4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]-triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Ethanol heptane	HCID 22502148	—
Reactant	4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one	HCID 91826330	—
Reactant	tert-butyl 3-(4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-6-oxo-5,6-dihydropyrrolo[3,4-c]pyrazol-1(4H)-yl)azetidine-1-carboxylate	HCID 117702723	—
Solvent	Diethyl Ether	HCID 3283	—
Product	(R)-4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]-triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one	HCID 91826392	—

Reaction Steps

The title compound (26 mg, 34% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: VWR prep HPLC; column: Chiralpak AD-H 20 μm, 76.5×393 mm; mobile phase: heptane/EtOH 60:40; flow: 80 mL/min; detection UV: 240 nm) of the racemic mixture of 4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 129) followed by trituration in diethyl ether.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08975417B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-04bb9092e065410d8a5d62b86d31ab00
Source note	uspto-grants-2015_03