HCID 91826322, compound → (R)-4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 874006Notes

Reaction equation

HRID 874006 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]([CH:56]4[CH2:58][CH2:57]4)[C:50]=3[C:49](=[O:59])[N:48]2[C:60]2[CH:61]=[C:62]([NH:70][CH3:71])[C:63]3[N:64]([C:66]([CH3:69])=[N:67][N:68]=3)[N:65]=2)=[CH:43][CH:42]=1>CCCCCCC.C(Cl)Cl.CCO>[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]([CH:56]4[CH2:57][CH2:58]4)[C:50]=3[C:49](=[O:59])[N:48]2[C:60]2[CH:61]=[C:62]([NH:70][CH3:71])[C:63]3[N:64]([C:66]([CH3:69])=[N:67][N:68]=3)[N:65]=2)=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 91826322HCID 91826322, compoundHCID 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 91826390(R)-4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

Reagents, catalysts & solvents 1

HCID 86658618Ethanol dichloromethane heptaneSolvent

Procedure

The title compound (38 mg, 34% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: Gilson PLC 2020; column: Chiralpak ID 5 μm, 20×250 mm; mobile phase: heptane/CH2Cl2/EtOH 70:25:5; flow: 10 mL/min; detection UV: 275 nm) of the racemic mixture of 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 113).

Sources & evidence

ORD record
ord-9e9873e1f0174337afa9a419ab189f8b
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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