Sodium hydride → HCID 19867668, compound

HRID 1199042Notes

Reaction equation

HRID 1199042 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11].[H-].[Na+].Cl[CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[N:28][C:29]([Cl:35])=[CH:30][CH:31]=2)[N:26]=1>O1CCCC1>[Cl:35][C:29]1[N:28]=[C:27]2[C:32]([CH:33]=[CH:34][C:25]([N:16]3[CH:15]([O:1][CH2:2][CH2:3][CH2:4][N:5]4[CH2:10][CH2:9][CH2:8][CH2:7][C:6]4=[O:11])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:24])=[N:26]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 574874HCID 574874, compoundHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 19867668HCID 19867668, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 22, but starting with N-(3-hydroxypropyl)-2-piperidone (7 g) in anhydrous tetrahydrofuran (150 cc), an oily suspension (50% by weight; 2.15 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (10 g). The product obtained is purified by chromatography on silica (0.063-0.2 mm; 240 g) contained in a column 5 cm in diameter, collecting 50-cc fractions. Fractions 23 to 27, eluted with a mixture of methylene chloride and methanol (95:5 by volume), are concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is crystallized by stirring in acetonitrile and then recrystallized in carbon tetrachloride. 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[3-(2-oxopiperidino)propoxy]-1-isoindolinone (2 g), m.p. 140° C., is thereby obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica (0.063-0.2 mm; 240 g)
  3. customcollecting 50-cc fractions
  4. washFractions 23 to 27, eluted with a mixture of methylene chloride and methanol (95:5 by volume)
  5. concentrationare concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  6. customThe residue obtained
  7. customis crystallized
  8. customrecrystallized in carbon tetrachloride

Sources & evidence

ORD record
ord-5f3eb5f6cbee4ec08b786847390900c7
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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