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

HRID 1029482Notes

Reaction equation

HRID 1029482 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.[C:23]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]1)(=[O:25])[CH3:24].N12CCCN=C1CCCCC2>CN(C)C=O>[C:23]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]([O:34][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:33])[CH2:28][CH2:27]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1172551-Acetylpiperidine-4-carboxylic acidHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 867456242-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 1-acetyl-4-piperidinecarboxylateYield 54.2%

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), 1-acetyl-4-piperidinecarboxylic acid (5.1 g) and 1,8-diazabicyclo-[5.4.0]-undec-7-ene (4.6 g), and after successive recrystallization in a mixture of acetone and water (2:1 by volume) and then in ethanol, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 1-acetyl-4-piperidinecarboxylate (7.5 g), m.p. 101° C., is obtained.

Workup

  1. customafter successive recrystallization
  2. additionin a mixture of acetone and water (2:1 by volume)

Sources & evidence

ORD record
ord-50cdaa35d16b4cbf934d282009552fb3
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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