Sodium hydride → HCID 19867680, compound

HRID 1199059Notes

Reaction equation

HRID 1199059 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5]1.[H-].[Na+].Cl[CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[N:17]1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[N:29][C:30]([Cl:36])=[CH:31][CH:32]=2)[N:27]=1>O1CCCC1>[C:10]([N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][O:1][CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]2[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[N:29][C:30]([Cl:36])=[CH:31][CH:32]=3)[N:27]=2)[CH2:5][CH2:6]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 47396291-Acetyl-4-(2-hydroxyethyl)piperazineHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 19867680HCID 19867680, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 22, but starting with 1-(2-hydroxyethyl)-4-acetylpiperazine (7.75 g) in anhydrous tetrahydrofuran (250 cc), an oily suspension (50% by weight; 2.3 g) of sodium hydride and 3-chloro-2(-7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (10 g). After crystallization successively in 2-propanol and then in ethanol, 3-[2-(4-acetyl-1-piperazinyl)ethoxy]-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (4.3 g), m.p. 172° C., is obtained.

Workup

  1. customAfter crystallization successively in 2-propanol

Sources & evidence

ORD record
ord-5190eb5d0891479fa83706965863be3e
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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