Dicyclohexylcarbodiimide → HCID 22917193, compound

HRID 1376507Notes

Reaction equation

HRID 1376507 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[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.ON1C2C=CC=CC=2N=N1.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][N:38]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([O:49][CH3:50])[CH:42]=2)[CH3:39])=[CH:32][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:39][N:38]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([O:49][CH3:50])[CH:42]=1)[CH2:37][CH2:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:16]([C:11]2[C:10]3[S: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:31][CH:32]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 4292989-Oxo-9H-thioxanthene-4-carboxylic acidHCID 10447541HCID 10447541, compound2×

Product 1

HCID 22917193HCID 22917193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 9-oxo-4-thioxanthenecarboxylic acid* (0.8 g) and 1-hydroxybenzotriazole (0.42 g) in DMF (20 ml) was stirred at room temperature for 10 min. 4-Amino-N-[(3,4-dimethoxyphenyl)methyl]-N-methylbenzenemethanamine (Intermediate 33(b) in EP-A-494623) (0.94 g) in DMF (20 ml) was then added, followed by dicyclohexylcarbodiimide (0.64 g) and the mixture was stirred at room temperature for 16 h and then filtered. The filtrate was concentrated in vacuo, treated with dilute sodium hydroxide solution and extracted with dichloromethane. The combined dried organic extracts were evaporated to leave an oil which was purified by column chromatography eluting with dichloromethane: methanol (95:5). The resulting solid was recrystallised from acetonitrile and filtered off to give the title compound as a solid (0.26 g),mp=180°.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with dilute sodium hydroxide solution
  5. extractionextracted with dichloromethane
  6. customwere evaporated
  7. customto leave an oil which
  8. customwas purified by column chromatography
  9. washeluting with dichloromethane: methanol (95:5)
  10. customThe resulting solid was recrystallised from acetonitrile
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-75c5118851a64803a1dee42d7c548ada
Source dataset
uspto-grants-1997_09
Patent number
US05663179

Reaction notes

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