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

HRID 874008Notes

Reaction equation

HRID 874008 reaction equation
ClC1C=CC(C2C3C(C)=NN(C4CN(C(OC(C)(C)C)=O)C4)C=3C(=O)N2C2C=C(C)C3N(C(C)=NN=3)C=2)=CC=1.CCCCCCC.CCO.[Cl:50][C:51]1[CH:56]=[CH:55][C:54]([CH:57]2[C:64]3[C:63]([CH:65]4[CH2:67][CH2:66]4)=[N:62][N:61]([CH3:68])[C:60]=3[C:59](=[O:69])[N:58]2[C:70]2[CH:71]=[C:72]([CH3:80])[C:73]3[N:74]([C:76]([CH3:79])=[N:77][N:78]=3)[CH:75]=2)=[CH:53][CH:52]=1>C(OCC)C>[Cl:50][C:51]1[CH:52]=[CH:53][C:54]([C@@H:57]2[C:64]3[C:63]([CH:65]4[CH2:67][CH2:66]4)=[N:62][N:61]([CH3:68])[C:60]=3[C:59](=[O:69])[N:58]2[C:70]2[CH:71]=[C:72]([CH3:80])[C:73]3[N:74]([C:76]([CH3:79])=[N:77][N:78]=3)[CH:75]=2)=[CH:55][CH:56]=1

Participants

5

Reactant 3

HCID 22502148Ethanol heptaneHCID 918263304-(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)-oneHCID 117702723tert-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

Product 1

HCID 91826392(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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Sources & evidence

ORD record
ord-04bb9092e065410d8a5d62b86d31ab00
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…