1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(7-Chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylate

HRID 1029477Notes

Reaction equation

HRID 1029477 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.Cl.[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=[O:32])[CH2:27][CH2:26]1.N12CCCN=C1CCCCC2>CN(C)C=O>[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:3]2[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=3)[N:13]=2)=[O:32])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 867456222-(7-Chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylateYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Working as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (9.9 g) in anhydrous dimethylformamide (100 cc), 1methyl-4-piperidinecarboxylic acid hydrochloride (5.4 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (10.7g), and after the residue obtained has been recrystallized twice successively in ethanol and then in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylate (5.6 g), m.p. 136° C. and then 157° C., is obtained.

Workup

  1. customafter the residue obtained
  2. customhas been recrystallized twice successively in ethanol

Sources & evidence

ORD record
ord-fb625c33ca80492e974c024b40f83042
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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