Trifluoroacetic acid → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-trifluoroacetylpiperazin-1-yl)carbonyloxy-isoindolin-1-one

HRID 27080Notes

Reaction equation

HRID 27080 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]([O:21][C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:30])=[N:9]2)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[F:46][C:47]([F:52])([F:51])[C:48](O)=[O:49]>C(Cl)Cl>[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:22]([N:24]4[CH2:25][CH2:26][N:27]([C:48](=[O:49])[C:47]([F:52])([F:51])[F:46])[CH2:28][CH2:29]4)=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:30])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 233436392-(7-Chloro-1,8-naphthyridin-2-yl)-3-(piperazin-1-yl)carbonyloxy-isoindolin-1-one

Product 1

HCID 137286412-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-trifluoroacetylpiperazin-1-yl)carbonyloxy-isoindolin-1-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 14 is followed but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(piperazin-1-yl)carbonyloxy-isoindolin-1-one (2.12 g.), N,N'-dicyclohexylcarbodiimide (2.05 g.) in anhydrous methylene chloride (50 cc.) and trifluoroacetic acid (1.71 g.). The crude product, after it has been filtered off, is washed with diethyl ether (50 cc.). The product is then dissolved in methylene chloride (110 cc.). The solution is filtered and concentrated to dryness and the residue is washed again with diethyl ether (45 cc.). 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-trifluoroacetylpiperazin-1-yl)carbonyloxy-isoindolin-1-one (0.91 g.), which melts at 218° C., is thus obtained.

Workup

  1. filtrationThe crude product, after it has been filtered off
  2. washis washed with diethyl ether (50 cc.)
  3. dissolutionThe product is then dissolved in methylene chloride (110 cc.)
  4. filtrationThe solution is filtered
  5. concentrationconcentrated to dryness
  6. washthe residue is washed again with diethyl ether (45 cc.)

Sources & evidence

ORD record
ord-6b6bfd40417a421b8b9433bcea2e7dc6
Source dataset
uspto-grants-1980_09
Patent number
US04220646

Reaction notes

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