Ethylenediamine → HCID 22467251, compound

HRID 1934604Notes

Reaction equation

HRID 1934604 reaction equation
C(SP([O-])(OCC)=S)C.[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([CH:19]([C:35]3[C:43]4[C:38](=[CH:39][C:40]([C:44]#[N:45])=[CH:41][CH:42]=4)[N:37]([CH3:46])[CH:36]=3)[C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:18][C:13]=2[O:12][CH2:11]1.[CH2:47](N)[CH2:48][NH2:49]>C(O)C.O>[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([CH:19]([C:35]3[C:43]4[C:38](=[CH:39][C:40]([C:44]5[NH:49][CH2:48][CH2:47][N:45]=5)=[CH:41][CH:42]=4)[N:37]([CH3:46])[CH:36]=3)[C:20]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:31]=3)(=[O:24])=[O:25])=[O:21])=[CH:18][C:13]=2[O:12][CH2:11]1

Participants

6

Reactant 3

HCID 3301Ethylenediamine2×HCID 22467231HCID 22467231, compound2×HCID 53249491Diethyldithiophosphate

Product 1

HCID 22467251HCID 22467251, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

Diethyldithiophosphate (1.3 ml, 7.7 mmol) was added to 3-{1-(1,3-benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl}-6-cyano-1-methyl-1H-indole (the product of Example 51, 800 mg, 1.5 mmol) in a mixture of ethanol (10 ml) and water (5 drops). The reaction was heated at reflux with stirring for 14 h. After cooling the solvent was removed in vacuo and the residues purified by flash column chromatography (elution with 98% dichloromethane/2% methanol) to give a brown oil. This residue was dissolved in ethylenediamine and the reaction mixture heated at reflux for 3 h. After cooling the ethylenediamine was removed in vacuo. Hydrochloric acid (10 ml) was added and the resulting precipitate was filtered and washed with dichloromethane and methanol. Flash column chromatography (elution with 80% dichloromethane/20% methanol/5% NH3) gave the product as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo
  5. customthe residues purified by flash column chromatography (elution with 98% dichloromethane/2% methanol)
  6. customto give a brown oil
  7. temperaturethe reaction mixture heated
  8. temperatureat reflux for 3 h
  9. customwas removed in vacuo
  10. additionHydrochloric acid (10 ml) was added
  11. filtrationthe resulting precipitate was filtered
  12. washwashed with dichloromethane and methanol
  13. washFlash column chromatography (elution with 80% dichloromethane/20% methanol/5% NH3)

Sources & evidence

ORD record
ord-3ea19de5609f4c13bea21ea0207d3572
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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