Pyridine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-one

HRID 66337

Reaction equation

[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[CH2:23]([N:25]([CH2:29][CH3:30])[C:26](Cl)=[O:27])[CH3:24].C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.O>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:26]([N:25]([CH2:29][CH3:30])[CH2:23][CH3:24])=[O:27])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The procedure of Example 21 is followed but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (6.2 g.) in methylene chloride (300 cc.), diethylcarbamoyl chloride (8.15 g.), triethylamine (8.4 cc.) and pyridine (30 cc.). Water (250 cc.) is added to the reaction mixture after it has been stirred for 48 hours at a temperature of about 20° C. The precipitate formed is filtered off and recrystallised from diisopropyl ether (800 cc.) to give 2-(7-chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-one (4.7 g.) melting at 142°-144° C.

Workup

customThe precipitate formed
filtrationis filtered off
customrecrystallised from diisopropyl ether (800 cc.)

Sources & evidence

ORD record: ord-5c9a789c3a32422c83bb9b1833d78db1
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04131674

Linked notes

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