4-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one → (R)-4-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 874007Notes

Reaction equation

HRID 874007 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]([CH2:55][O:56][CH3:57])=[N:52][N:51]([CH:58]4[CH2:60][CH2:59]4)[C:50]=3[C:49](=[O:61])[N:48]2[C:62]2[CH:67]=[C:66]([CH3:68])[C:65](=[O:69])[N:64]([CH3:70])[CH:63]=2)=[CH:43][CH:42]=1>CCCCCCC.CC(O)C>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]2[C:54]3[C:53]([CH2:55][O:56][CH3:57])=[N:52][N:51]([CH:58]4[CH2:60][CH2:59]4)[C:50]=3[C:49](=[O:61])[N:48]2[C:62]2[CH:67]=[C:66]([CH3:68])[C:65](=[O:69])[N:64]([CH3:70])[CH:63]=2)=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 918263334-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-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 91826360(R)-4-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

The title compound (32 mg, 42% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: Gilson PLC 2020; column: Chiralcel OD-H 5 μm, 20×250 mm; mobile phase: heptane/iPrOH 80:20; flow: 10 mL/min; detection UV: 210 nm) of the racemic mixture of 4-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 132).

Sources & evidence

ORD record
ord-61d2ce2963b74ace92b3e733bdaa458b
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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