Dimethylformamide → [2-(7-bromo-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-N-propylglycolamide

HRID 1199062

Reaction equation

[Br:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=O)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25]([NH:28][C:29](=[O:32])[CH2:30]Cl)[CH2:26][CH3:27].CN(C)C=[O:36]>>[Br:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH:30]([OH:36])[C:29]([NH:28][CH2:25][CH2:26][CH3:27])=[O:32])=[N:9]2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 2223572-chloro-N-propylacetamide

HCID 199004212-(7-Bromo-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

Product 1

HCID 19867687[2-(7-bromo-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-N-propylglycolamide

Procedure

The procedure is as in Example 26, but starting with 2-(7-bromo-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (12 g) in anhydrous dimethylformamide (300 cc), an oily suspension (50% by weight; 2.4 g) of sodium hydride and N-(propyl)chloroacetamide (6.9 g). After recrystallization in acetonitrile, [2-(7-bromo-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-N-propylglycolamide (2.1 g), m.p. 174° C., is obtained.

Workup

customAfter recrystallization in acetonitrile

Sources & evidence

ORD record: ord-d4f985c2d61648a1ab96336c24aeb34f
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898871

Linked notes

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