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Pyridine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-6-trifluoromethyl-isoindolin-1-one

HRID 66344
Notes
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Reaction equation

HRID 66344 reaction equation
N1C=CC=CC=1.[CH2:7]([N:11]=[C:12]=[O:13])[CH2:8][CH2:9][CH3:10].[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([OH:34])[C:32]4[C:27](=[CH:28][C:29]([C:35]([F:38])([F:37])[F:36])=[CH:30][CH:31]=4)[C:26]3=[O:39])=[N:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(#N)C>[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([O:34][C:12]([NH:11][CH2:7][CH2:8][CH2:9][CH3:10])=[O:13])[C:32]4[C:27](=[CH:28][C:29]([C:35]([F:37])([F:38])[F:36])=[CH:30][CH:31]=4)[C:26]3=[O:39])=[N:22]2)=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 227547182-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxy-6-trifluoromethyl-1-isoindolinone

Product 1

HCID 227547542-(7-Chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-6-trifluoromethyl-isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine (10 cc.) and butyl isocyanate (11.2 cc.) are added to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-6-trifluoromethyl-isoindolin-1-one (3.8 g.) in acetonitrile (380 cc.). The mixture is heated to the reflux temperature and triethylamine (0.5 cc.) is added. Refluxing is continued for 50 minutes until dissolution. After cooling the solution, the precipitate formed is filtered off and washed with water (30 cc.). After drying, a first crop of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-6-trifluoromethyl-isoindolin-1-one (2.8 g.) is obtained.

Workup

  1. additionis added
  2. temperatureRefluxing
  3. dissolutionis continued for 50 minutes until dissolution
  4. temperatureAfter cooling the solution
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water (30 cc.)
  8. customAfter drying

Sources & evidence

ORD record
ord-48265dc15ee1448e807c41b69845e4ad
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04131674

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes