Dicyclohexylcarbodiimide → N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

HRID 1451644Notes

Reaction equation

HRID 1451644 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16](O)=[O:17])[C:10]=2[NH:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.ON1C2C=CC=CC=2N=N1.[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:16]([C:11]2[C:10]3[NH:9][C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2](=[O:1])[C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:17])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 35607584-Carboxy-9-acridanoneHCID 199745634-(3-Bromopropoxy)aniline

Product 1

HCID 15299131N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9,10-dihydro-9-oxo-4-acridinecarboxylic acid (1.5 g) and 1-hydroxybenzotriazole (1.1 g) in DMF (50 ml) was stirred at room temperature for 10 min. The product of part (ii) above (1.5 g) was then added followed by dicyclohexylcarbodiimide (1.3 g), and the mixture was stirred at room temperature for 16 h and then filtered. The filtrate was concentrated in vacuo, treated with water and extracted with dichloromethane. The combined, dried organic extracts were concentrated to give the title compound (0.5 g) which was recrystallised from acetonitrile, MP 126°.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with water
  5. extractionextracted with dichloromethane
  6. concentrationdried organic extracts were concentrated

Sources & evidence

ORD record
ord-87016f6b3580417eabca14c9e3f9c9a1
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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