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1-Methylpiperazine → 3-(4-Methylpiperazin-1-yl)carbonyloxy-5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)isoindolin-1-one

HRID 259650
Notes
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Reaction equation

HRID 259650 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]([O:24]C4C=CC=CC=4)=O)[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([Cl:31])[CH:18]=4)[C:13]3=[O:32])=[N:9]2)=[CH:4][CH:3]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>C(#N)C.C(Cl)Cl.C(OCC)(=O)C>[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([C:22]([O:21][CH:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:31])[CH:18]=3)[C:13](=[O:32])[N:12]2[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)=[O:24])[CH2:36][CH2:35]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 531671-MethylpiperazineHCID 214221182-(7-Chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-5-chloro-isoindolin-1-one

Product 1

HCID 214220803-(4-Methylpiperazin-1-yl)carbonyloxy-5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)isoindolin-1-oneYield 59.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent
HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

The procedure of Example 11 is followed but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-5-chloro-3-phenoxycarbonyloxy-isoindolin-1-one (1.25 g.) and 4-methylpiperazine (1.07 g.) in acetonitrile (33 cc.) and stirring for 24 hours at a temperature of about 20° C. From the reaction mixture, the resulting precipitate is filtered off and washed successively with acetonitrile (6 cc.) and diethyl ether (6 cc.). The product obtained (0.93 g.) is dissolved in methylene chloride (35 cc.), and the solution passed through a column of silica gel (10 g.). Elution is carried out with methylene chloride (16 × 20 cc.); the corresponding eluates are discarded. Elution is the carried out with ethyl acetate (5 × 20 cc.); the corresponding eluates are combined and concentrated under reduced pressure. A crystalline residue (0.9 g.) is obtained and is suspended in ethyl acetate (20 cc.). The crystals are filtered off and dried to yield 3-(4methylpiperazin-1-yl)carbonyloxy-5-chloro- 2-(7-chloro-1,8-naphthyridin-2-yl)isoindolin-1-one (0.75 g.) melting at 255° C.

Workup

  1. filtrationFrom the reaction mixture, the resulting precipitate is filtered off
  2. washwashed successively with acetonitrile (6 cc.) and diethyl ether (6 cc.)
  3. customThe product obtained (0.93 g.)
  4. washElution
  5. washElution
  6. concentrationconcentrated under reduced pressure
  7. customA crystalline residue (0.9 g.) is obtained
  8. filtrationThe crystals are filtered off
  9. customdried

Sources & evidence

ORD record
ord-9266017d9a0b42aeb5ee0ac87950f74b
Source dataset
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04038391

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes