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

HRID 66342Notes

Reaction equation

HRID 66342 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][CH:29]=[C:30]([C:35]([F:38])([F:37])[F:36])[CH:31]=4)[C:26]3=[O:39])=[N:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(#N)C>[CH2:7]([NH:11][C:12]([O:34][CH:33]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:35]([F:37])([F:38])[F:36])[CH:31]=2)[C:26](=[O:39])[N:25]1[C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[N:24][C:15]([Cl:14])=[CH:16][CH:17]=2)[N:22]=1)=[O:13])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 227547132-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxy-5-trifluoromethyl-isoindolin-1-one

Product 1

HCID 227547593-n-Butylaminocarbonyloxy-2-(7-chloro-1,8-naphthyridin-2-yl)-5-trifluoromethyl-isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine (10 cc.) and n-butyl isocyanate (11.2 cc.) are added to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-5-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 then added. Refluxing is continued for 1 hour and 30 minutes until dissolution. The reaction mixture is then concentrated under reduced pressure (40 mm.Hg), and the residue is recrystallised from acetonitrile (48 cc.) to give 3-n-butylaminocarbonyloxy-2-(7-chloro-1,8-naphthyridin-2-yl)-5-trifluoromethyl-isoindolin-1-one (3.5 g.) melting at 120° C. and then at 176° C.

Workup

  1. additionis then added
  2. temperatureRefluxing
  3. dissolutionis continued for 1 hour and 30 minutes until dissolution
  4. concentrationThe reaction mixture is then concentrated under reduced pressure (40 mm.Hg)
  5. customthe residue is recrystallised from acetonitrile (48 cc.)

Sources & evidence

ORD record
ord-8febc95d8af146de827d87a7e8647bbe
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

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