Potassium Carbonate → HCID 10316915, compound

HRID 128835Notes

Reaction equation

HRID 128835 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5]2[C:10]([C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])=[C:3]1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 11780998HCID 11780998, compound

Product 1

HCID 10316915HCID 10316915, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(methylthio)-N-phenyl-1H-indole-3-carboxamide [XXV: R8 =H] (1.8 g, 6.4 mmol) in EtOH (400 mL) was treated with 3-(dimethylamino)propyl chloride hydrochloride (10.0 g, 64 mmol) and K2CO3 (13 g, 96 mmol) and heated under reflux for 3 hours. A further 10 equivalents of the reagents were then added, and the mixture was heated under reflux for a further 48 hours. EtOH was removed under reduced pressure, and the residue was diluted with water to give crude product. This was chromatographed on alumina, eluting with CH2Cl2 containing 0.2% MeOH, to give 1-[3-(dimethylamino)propyl] -2-(methylthio)-N-phenyl-1H-indole-3-carboxamide [XXVI: R8 =H, R9 =(CH2)3NMe2 ] (0.49 g, 21%) as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 48 hours
  5. customEtOH was removed under reduced pressure
  6. additionthe residue was diluted with water
  7. customto give crude product
  8. customThis was chromatographed on alumina
  9. washeluting with CH2Cl2 containing 0.2% MeOH

Sources & evidence

ORD record
ord-a045b8bda58c4bccb8ac82c00c0ba269
Source dataset
uspto-grants-1995_11
Patent number
US05464861

Reaction notes

Loading…