Sodium Azide → HCID 19696341, compound

HRID 863680Notes

Reaction equation

HRID 863680 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[CH2:37][CH2:36][N:11]2[C:12]3[C:17]([C:18]([C:19]4[C:20](=[O:35])[NH:21][C:22](=[O:34])[C:23]=4[C:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]([CH3:33])[CH:25]=4)=[C:10]2[CH2:9]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(=O)=O.[N-:38]=[N+:39]=[N-:40].[Na+]>CN(C)C=O>[N:38]([CH2:6][CH2:7][CH:8]1[CH2:37][CH2:36][N:11]2[C:12]3[C:17]([C:18]([C:19]4[C:20](=[O:35])[NH:21][C:22](=[O:34])[C:23]=4[C:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]([CH3:33])[CH:25]=4)=[C:10]2[CH2:9]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N+:39]=[N-:40]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19696325HCID 19696325, compound

Product 1

HCID 19696341HCID 19696341, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 500 mg of the pyrroledione product of Example 15 and 250 mg of sodium azide in 10 ml of dimethylformamide was heated at 70° C. for 3 hours. The solvent was removed by evaporation and the solid was partitioned between ethyl acetate and water. The insoluble material was filtered off and dried to give 425 mg of 3-[8-(2-azidoethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 262°-264° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe solid was partitioned between ethyl acetate and water
  3. filtrationThe insoluble material was filtered off
  4. customdried

Sources & evidence

ORD record
ord-7972d0ae91074888a39a130e83d5809c
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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