2-[(2S)-1-Hydroxy-4-methylpentan-2-yl]-1H-isoindole-1,3(2H)-dione → (S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione

HRID 1398387Notes

Reaction equation

HRID 1398387 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.[OH:19][CH2:20][C@@H:21]([N:26]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36])[CH2:22][CH:23]([CH3:25])[CH3:24]>>[CH3:15][C:10]1[N:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8](=[O:16])[N:7]([CH3:17])[C:6]1[CH:18]=[C:2]([O:19][CH2:20][C@@H:21]([N:26]3[C:27](=[O:36])[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]3=[O:35])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH:3]=[CH:4][C:5]2=1

Participants

3

Reactant 2

HCID 713789222-[(2S)-1-Hydroxy-4-methylpentan-2-yl]-1H-isoindole-1,3(2H)-dioneHCID 867103378-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one

Product 1

HCID 86710374(S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dioneYield 49%

Procedure

8-Chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.4 g, 5.41 mmol) and (S)-2-(1-hydroxy-4-methylpentan-2-yl)isoindoline-1,3-dione (4.01 g, 16.23 mmol) were subjected to Buchwald coupling as described in Example 16, Part H) to give (S)-2-(1-((4,6-dimethyl-5-oxo 5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)isoindoline-1,3-dione as yellow solid (1.4 g, 2.62 mmol, 49% yield). LC/MS (ESI) m/e 470.2 [(M+H)+, calcd for C28H28N3O4 470.2]; LC/MS retention time (method C): tR=2.05 min.

Sources & evidence

ORD record
ord-ebb0125c28944f5c84f9be83705d81ca
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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