4-(4-chloro-2-fluorophenyl)-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-(4-chloro-2-fluorophenyl)-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 874012Notes

Reaction equation

HRID 874012 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.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]2[C:54]3[C:53]([CH3:55])=[N:52][N:51]([CH2:56][CH3:57])[C:50]=3[C:49](=[O:58])[N:48]2[C:59]2[CH:60]=[C:61]([CH3:69])[C:62]3[N:63]([C:65]([CH3:68])=[N:66][N:67]=3)[CH:64]=2)=[C:43]([F:70])[CH:42]=1>CC(O)C>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]2[C:54]3[C:53]([CH3:55])=[N:52][N:51]([CH2:56][CH3:57])[C:50]=3[C:49](=[O:58])[N:48]2[C:59]2[CH:60]=[C:61]([CH3:69])[C:62]3[N:63]([C:65]([CH3:68])=[N:66][N:67]=3)[CH:64]=2)=[C:43]([F:70])[CH:42]=1

Participants

4

Reactant 2

HCID 918263784-(4-chloro-2-fluorophenyl)-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 91826385(S)-4-(4-chloro-2-fluorophenyl)-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 3776IsopropanolSolvent

Procedure

The title compound (52 mg, 47% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: MGII preparative SFC; column: Chiralpak AD-H, 30×250 mm; mobile phase: scCO2/iPrOH 60:40; flow: 50 mL/min; temperature: 38° C.; detection UV: 220 nm) of the racemic mixture of 4-(4-chloro-2-fluorophenyl)-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 185).

Sources & evidence

ORD record
ord-67c829c669fd4cea9fa55d3df56dce53
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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