Methanol → HCID 178434175, compound

HRID 874009Notes

Reaction equation

HRID 874009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12](C4CN(C(OC(C)(C)C)=O)C4)[C:11]=3[C:10](=[O:28])[N:9]2[C:29]2[CH:30]=[C:31]([CH3:39])[C:32]3[N:33]([C:35]([CH3:38])=[N:36][N:37]=3)[CH:34]=2)=[CH:4][CH:3]=1.CO.ClC1C=CC(C2C3C(C4CC4)=NNC=3C(=O)N2C2C=C(C)C3N(C(C)=NN=3)C=2)=CC=1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C:15]3[C:14]([CH3:16])=[N:13][NH:12][C:11]=3[C:10](=[O:28])[N:9]2[C:29]2[CH:30]=[C:31]([CH3:39])[C:32]3[N:33]([C:35]([CH3:38])=[N:36][N:37]=3)[CH:34]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 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-carboxylateHCID 178428082HCID 178428082, compound

Product 1

HCID 178434175HCID 178434175, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound (133 mg, 44% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative SFC (system: Thar SFC200; column: Chiralpak OD-H, 30×250 mm; mobile phase: scCO2/MeOH 70:30; flow: 120 g/min; detection UV: 265 nm) of the racemic mixture of 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 129) and subsequent trituration in diethyl ether.

Sources & evidence

ORD record
ord-4b2e229773b840c98fb288c55134e133
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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