Pyridine → 5-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one

HRID 66345Notes

Reaction equation

HRID 66345 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:28]=[CH:27][C:26]3[C:21](=[N:22][C:23]([Cl:29])=[CH:24][CH:25]=3)[N:20]=1)[CH:12]2[OH:30].N1C=CC=CC=1>C(#N)C.C(N(CC)CC)C>[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:28]=[CH:27][C:26]3[C:21](=[N:22][C:23]([Cl:29])=[CH:24][CH:25]=3)[N:20]=1)[CH:12]2[O:30][C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8110Butyl isocyanateHCID 198422422-(7-Chloro-1,8-naphthyridin-2-yl)-5-chloro-3-hydroxy-isoindolin-1-one

Product 1

HCID 867356475-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent2×

Procedure

n-Butyl isocyanate (11.2 cc.) is added over the course of 15 minutes to a suspension of 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (3.5 g.) in acetonitrile (350 cc.) and triethylamine (0.2 cc.) heated at the reflux temperature. Pyridine (10 cc.) and triethylamine (5 cc.) are added and refluxing is continued for a further 40 minutes. After filtering hot and then cooling, the precipitate formed is filtered off and recrystallised from acetonitrile (250 cc.) to give 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one (3.3 g.) melting at 228°-230° C.

Workup

  1. temperatureheated at the reflux temperature
  2. temperaturerefluxing
  3. filtrationAfter filtering hot
  4. temperaturecooling
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. customrecrystallised from acetonitrile (250 cc.)

Sources & evidence

ORD record
ord-2368399e39304d308304ff048f1fcfef
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

Loading…