Sodium hydride → HCID 19867693, compound

HRID 1199041Notes

Reaction equation

HRID 1199041 reaction equation
[CH:1]([NH:4][C:5](=[O:8])[CH2:6][OH:7])([CH3:3])[CH3:2].[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][CH:1]([CH3:3])[CH3:2])=[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 1588113538052-77-6

Product 1

HCID 19867693HCID 19867693, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 22, but starting with N-isopropylglycolamide (5.3 g) in tetrahydrofuran (250 cc), an oily suspension (50% by weight; 2.2 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (10 g). After purification by recrystallization in acetonitrile, [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]-N-isopropylacetamide (4 g), m.p. 188° C., is obtained.

Workup

  1. customAfter purification
  2. customby recrystallization in acetonitrile

Sources & evidence

ORD record
ord-920b64c0dd9548d8819b45e2c43bcac9
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

Loading…