Methane → 2-(7-Chloro-1,8 naphtyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one

HRID 66340Notes

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:27]=[C:28]=[O:29])[CH2:24][CH2:25][CH3:26].C>C(#N)C>[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:28]([NH:27][CH2:23][CH2:24][CH2:25][CH3:26])=[O:29])[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

A mixture of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (1.56 g.) and n-butyl isocyanate (0.99 g.) in anhydrous acetonitrile (30 cc.) is heated at the reflux temperature for 2 hours. The solution obtained is treated with decolourising charcoal at the reflux temperature, filtered hot, after which it is cooled to a temperature of about 20° C. The product which crystallises is filtered off and washed with acetonitrile (4 cc.). After drying, 2-(7-chloro-1,8 naphtyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one (0.96 g.), melting at 152° C. and then at 174° C., is obtained.

Workup

temperatureis heated at the reflux temperature for 2 hours
customThe solution obtained
filtrationfiltered hot
customThe product which crystallises
filtrationis filtered off
washwashed with acetonitrile (4 cc.)
customAfter drying

Sources & evidence

ORD record: ord-e993f3a3b3f54538b177d9e685e5ddf6
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04131674

Reaction notes

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