1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86745627, compound

HRID 1029495Notes

Reaction equation

HRID 1029495 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].Cl[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1.N12CCCN=C1CCCCC2>CN(C)C=O>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1)=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4399035-(Acetylamino)pentanoic acidHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 86745627HCID 86745627, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 24, but starting with 5-acetamidopentanoic acid (5 g) in dimethylformamide (66 cc), 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (6.6 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.7 cc). After recrystallization in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 5-acetamidopentanoate (3.3 g), m.p. 185° C., is obtained.

Workup

  1. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-f660f4e2c3cc42dd9b39f0016cddc25c
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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