1,1'-Carbonyldiimidazole → HCID 18412364, compound

HRID 50238Notes

Reaction equation

HRID 50238 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11](O)=O)=[CH:5][CH:4]=1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][N:27]([CH:40]1[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]1)[S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][CH3:38])=[C:33]([NH2:39])[CH:32]=1)(=[O:30])=[O:29].ClCCl.C(O)C>O1CCCC1>[CH3:26][N:27]([CH:40]1[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]1)[S:28]([C:31]1[CH:36]=[CH:35][C:34]2[N:37]([CH3:38])[C:11]([CH2:10][O:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:39][C:33]=2[CH:32]=1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 7360972-(4-Cyanophenoxy)acetic acidHCID 18412481HCID 18412481, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 18412364HCID 18412364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

532 mg (3.0 mmol) of 4-cyanophenyloxyacetic acid and 486 mg (3.0 mmol) of 1,1′-carbonyldiimidazole were dissolved in 40 mL of tetrahydrofuran and refluxed for 15 minutes. Then 700 mg (2.24 mmol) of 3-amino-4-methylaminobenzenesulfonic acid-N-methyl-N-(1-methylpiperidin-4-yl)amide were added and boiling was continued for a further eight hours. Then the mixture was evaporated down and the resulting oily residue was refluxed in 30 mL of glacial acetic acid for one hour. The glacial acetic acid was distilled off, the residue was mixed with about 30 mL of water and made alkaline with concentrated ammonia, and the solution was extracted three times with about 20 mL of dichloromethane. The organic phases were dried and evaporated down. The resulting product was further reacted without any purification. Yield: 400 mg (39% of theory), C23H27N5O3S (453.6); Rf value: 0.37 (silica gel; dichloromethane/ethanol=4:1).

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThen the mixture was evaporated down
  3. temperaturethe resulting oily residue was refluxed in 30 mL of glacial acetic acid for one hour
  4. distillationThe glacial acetic acid was distilled off
  5. additionthe residue was mixed with about 30 mL of water
  6. extractionthe solution was extracted three times with about 20 mL of dichloromethane
  7. customThe organic phases were dried
  8. customevaporated down
  9. customThe resulting product was further reacted without any purification

Sources & evidence

ORD record
ord-ac2e42d91d6d4afc8a47e5b2472035da
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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