4-(2,4-difluorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one → (S)-4-(2,4-difluorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 874011Notes

Reaction equation

HRID 874011 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.[F:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[CH:48]1[C:55]2[C:54]([CH3:56])=[N:53][N:52]([CH2:57][CH3:58])[C:51]=2[C:50](=[O:59])[N:49]1[C:60]1[CH:61]=[C:62]([CH3:70])[C:63]2[N:64]([C:66]([CH3:69])=[N:67][N:68]=2)[CH:65]=1>CCCCCCC.CCO.CO>[F:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[C@@H:48]1[C:55]2[C:54]([CH3:56])=[N:53][N:52]([CH2:57][CH3:58])[C:51]=2[C:50](=[O:59])[N:49]1[C:60]1[CH:61]=[C:62]([CH3:70])[C:63]2[N:64]([C:66]([CH3:69])=[N:67][N:68]=2)[CH:65]=1

Participants

4

Reactant 2

HCID 918263744-(2,4-difluorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethyl-3-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 91826384(S)-4-(2,4-difluorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Reagents, catalysts & solvents 1

HCID 22386818heptane EtOH MeOHSolvent

Procedure

The title compound (34 mg, 48% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: Gilson PLC 2020; column: Chiralpak AD-H, 20×250 mm; mobile phase: heptane/EtOH/MeOH 80:10:10; flow: 12 mL/min; temperature: 38° C.; detection UV: 220 nm) of the racemic mixture of 4-(2,4-difluorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 181).

Sources & evidence

ORD record
ord-f84a890b1b154473935751365f64d4d8
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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