Sodium hydride → HCID 21422099, compound

HRID 328269Notes

Reaction equation

HRID 328269 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH:19]([OH:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].[H-].[Na+].Cl[C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)=[O:26]>O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:33][N:30]1[CH2:31][CH2:32][N:27]([C:25]([O:21][CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19](=[O:20])[N:11]2[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[N:7][CH:6]=3)[N:1]=2)=[O:26])[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 21422072HCID 21422072, compound

Product 1

HCID 21422099HCID 21422099, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

Following the procedure of Example 4 but starting with 2-(1,6-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (1.7 g.) in anhydrous tetrahydrofuran (17 cc.), sodium hydride (50% dispersion in mineral oil) (0.58 g.), 1-chlorocarbonyl-4-methylpiperazine (0.5 g.) in anhydrous tetrahydrofuran (5 cc.) and hexamethylphosphotriamide (4.5 cc.), a product (1.3 g.), melting at 215° C., is obtained. After washing with diisopropyl ether (30 cc.), this product is dissolved in methylene chloride (40 cc.). After filtration, the solution is concentrated to dryness to yield 3-(4-methylpiperazin-1-yl)carbonyloxy-2-(1,6-naphthyridin-2-yl)isoindolin-1-one (1 g.) melting at 215° C.

Workup

  1. washAfter washing with diisopropyl ether (30 cc.)
  2. dissolutionthis product is dissolved in methylene chloride (40 cc.)
  3. filtrationAfter filtration
  4. concentrationthe solution is concentrated to dryness

Sources & evidence

ORD record
ord-f2029d98bdba46c6a06e23f39ebf1f4b
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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