Sodium Hydroxide → 2-{1-[(7-Chloro-1,8-naphthyridin-2-yl)amino]-6-methyl-3-oxoheptyl}benzoic acid

HRID 1440306Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH:22]([C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])C(O)=O)=[N:9]2)=[CH:4][CH:3]=1.[OH-:33].[Na+]>O>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH:12][CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:20]([OH:21])=[O:33])[CH2:22][C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 30 mg of (±)-2-[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoic acid in 4.7 cm3 of distilled water and 1.32 cm3 of a 0.1N aqueous sodium hydroxide solution is stirred at a temperature of approximately 20° C. for 72 hours. An insoluble product is removed by filtration and the filtrate is acidified to a pH=2 by addition of a 0.1N aqueous hydrochloric acid solution. The precipitate obtained is separated by filtration, washed with water and dried in air. 10 mg of (±)-2-{1-[(7-chloro-1,8-naphthyridin-2-yl)amino]-6-methyl-3-oxoheptyl}benzoic acid are thus obtained whose characteristics are identical to those of the product of Example 1.

Workup

customAn insoluble product is removed by filtration
additionthe filtrate is acidified to a pH=2 by addition of a 0.1N aqueous hydrochloric acid solution
customThe precipitate obtained
customis separated by filtration
washwashed with water
customdried in air

Sources & evidence

ORD record: ord-c056f0b9b2854032983d2e7383d78e55
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05498716

Reaction notes

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