5-Methylhexanoic acid → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 5-methylhexanoate

HRID 1029483Notes

Reaction equation

HRID 1029483 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.[CH3:23][CH:24]([CH3:31])[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].N12CCCN=C1CCCCC2>CN(C)C=O>[CH3:23][CH:24]([CH3:31])[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1)=[O:29]

Participants

5

Reactant 3

HCID 123445-Methylhexanoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 199004272-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 5-methylhexanoateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Working as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2yl)-1-isoindolinone (9.9 g) in anhydrous dimethylformamide (100 cc), 5-methylhexanoic acid (3.9 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g), and after recrystallization in ethanol, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 5-methylhexanoate (8 g), m.p. 132° C., is obtained.

Workup

  1. customafter recrystallization in ethanol

Sources & evidence

ORD record
ord-0be8b216e98644b0bd42050b65c99eb0
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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