Sodium hydride → HCID 19867660, compound

HRID 1199045Notes

Reaction equation

HRID 1199045 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][NH:4][C:5](=[O:8])[CH2:6][OH:7].[H-].[Na+].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>O1CCCC1>[Cl:33][C:27]1[N:26]=[C:25]2[C:30]([CH:31]=[CH:32][C:23]([N:14]3[C:15](=[O:22])[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:13]3[O:7][CH2:6][C:5]([NH:4][CH2:3][CH:2]([CH3:9])[CH3:1])=[O:8])=[N:24]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 198676532-Hydroxy-N-(2-methylpropyl)acetamide

Product 1

HCID 19867660HCID 19867660, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 22, but starting with N-(2-methylpropyl)glycolamide (8.9 g) in tetrahydrofuran (357 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 ethanol, [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1isoindolinyloxy]-N-(2-methylpropyl)acetamide (10.1 g), m.p. 146° C., is obtained.

Workup

  1. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-dea3083db9d342138e16e3a8da3814a8
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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