Dicyclohexylcarbodiimide → HCID 86587853, compound

HRID 1375317Notes

Reaction equation

HRID 1375317 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH:9]1[C:22]2[C:13](=[N:14][C:15]3[C:20]([C:21]=2[C:23]([O:25][C:26]2[C:31]([Br:32])=[CH:30][C:29]([CH2:33][CH2:34][C:35](O)=[O:36])=[CH:28][C:27]=2[Br:38])=[O:24])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:19]1[C:20]2[C:15](=[N:14][C:13]3[C:22]([C:21]=2[C:23]([O:25][C:26]2[C:27]([Br:38])=[CH:28][C:29]([CH2:33][CH2:34][C:35]([O:1][N:2]4[C:6](=[O:7])[CH2:5][CH2:4][C:3]4=[O:8])=[O:36])=[CH:30][C:31]=2[Br:32])=[O:24])=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 86587851HCID 86587851, compound

Product 1

HCID 86587853HCID 86587853, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

N-Hydroxysuccinimide (12 mg, 0.10 mmol) and 2,6-dibromo-4-(2-carboxyethyl)phenyl acridine-9-carboxylate (50 mg, 0.090 mmol) were dissolved in anhydrous DMF (3 ml) and cooled to −20° C. Dicyclohexylcarbodiimide (DCC, 22 mg, 0.11 mmol) was added and the mixture was stirred at −20° C. for 2 h. The solution was stirred overnight at room temperature, and then evaporated to dryness. The residue was extracted with dichloromethane (50 ml) and the filtrate was evaporated to obtain the crude product (100 mg). Further purification was carried out by chromatotron, eluted with chloroform. The solvent was evaporated from the appropriate combined fractions to give the desired product as a light-brown solid (40 mg, 64%), mp 175–6° C. FAB-MS m/z 627 [(M+1)+, 20%], 225 [100], 206 [18], 179 [10], 143 [8].

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. customevaporated to dryness
  3. extractionThe residue was extracted with dichloromethane (50 ml)
  4. customthe filtrate was evaporated
  5. customto obtain the crude product (100 mg)
  6. customFurther purification
  7. washeluted with chloroform
  8. customThe solvent was evaporated from the appropriate combined fractions

Sources & evidence

ORD record
ord-a9767a0fb27c4cb58bf1b79384dee762
Source dataset
uspto-grants-2007_01
Patent number
US07169554B2

Reaction notes

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