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

HRID 1029485Notes

Reaction equation

HRID 1029485 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:27]1[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]1)(=[O:26])[CH2:24][CH3:25].N12CCCN=C1CCCCC2>CN(C)C=O>[C:23]([N:27]1[CH2:28][CH2:29][CH:30]([C:33]([O:35][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:34])[CH2:31][CH2:32]1)(=[O:26])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6851551-Propionyl-4-piperidinecarboxylic acidHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 199004062-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 1-propionyl-4-piperidinecarboxylateYield 34.5%

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-propionyl-4-piperidinecarboxylic acid (5.5 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g), and by recrystallization in ethanol, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 1-propionyl-4-piperidinecarboxylate (4.9 g), m.p. 189° C., is obtained.

Workup

  1. customby recrystallization in ethanol

Sources & evidence

ORD record
ord-eed50f1ea10d4526885712acad440d83
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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