Sodium hydride → HCID 86743740, compound

HRID 1199044Notes

Reaction equation

HRID 1199044 reaction equation
[CH2:1]([NH:4][C:5](=[O:8])[CH2:6][OH:7])[CH2:2][CH3:3].[H-].[Na+].Cl[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[N:25][C:26]([Cl:32])=[CH:27][CH:28]=2)[N:23]=1>O1CCCC1>[Cl:32][C:26]1[N:25]=[C:24]2[C:29]([CH:30]=[CH:31][C:22]([N:13]3[C:14](=[O:21])[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]3[O:7][CH2:6][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:8])=[N:23]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 19867655HCID 19867655, compound

Product 1

HCID 86743740HCID 86743740, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 22, but starting with N-propylglycolamide (9.4 g) in tetrahydrofuran (375 cc), an oily suspension (50% by weight; 3.3 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (15 g). After recrystallization in acetonitrile, [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1isoindolinyloxy]-N-propylacetamide (10.5 g), m.p. 167° C., is obtained.

Workup

  1. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-34040fd966774e968f289ebd77fdc026
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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