Diisopropyl Ether → HCID 21444385, compound

HRID 328273Notes

Reaction equation

HRID 328273 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([N:12]1[CH:20]([O:21][C:22]([O:24]C3C=CC=CC=3)=O)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]1=[O:31])=[N:7]2.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(OC(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([N:12]1[CH:20]([O:21][C:22]([N:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)=[O:24])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]1=[O:31])=[N:7]2

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 531671-MethylpiperazineHCID 214220742-(5-Chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one

Product 1

HCID 21444385HCID 21444385, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

The procedure of Example 11 is followed but starting with 2-(5-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (6.7 g.), 4-methylpiperazine (15.8 g.) and dimethylformamide (32 cc.) and stirring for 15 minutes at 23° C. The reaction mixture is then diluted by adding diisopropyl ether (320 cc.). The precipitate is filtered off, washed with diisopropyl ether (3 × 30 cc.) and then dried. A product (3.8 g.) is obtained which is recrystallised from acetonitrile (300 cc.) to yield 2-(5-chloro-1,8-naphthyridin-2yl)-3-(4-methylpiperazin-1-yl)carbonyloxy-isoindolin-1-one (2.9 g.) melting at 240° C.

Workup

  1. additionThe reaction mixture is then diluted
  2. filtrationThe precipitate is filtered off
  3. washwashed with diisopropyl ether (3 × 30 cc.)
  4. customdried
  5. customA product (3.8 g.) is obtained which
  6. customis recrystallised from acetonitrile (300 cc.)

Sources & evidence

ORD record
ord-acb816f11bc9441494eb9000e3b0f84a
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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