Pyridine → HCID 22754754, compound

HRID 2083745Notes

Reaction equation

HRID 2083745 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

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 22754754HCID 22754754, compound

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-e5b2f2a795c84f8e854da4b6da740285
Source dataset
uspto-grants-1978_04
Patent number
US04086348

Reaction notes

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