Dimethylformamide → 1-(3-Dimethylaminobutyl)-3-(3-diethylaminopropylamino)-5-chloroindazole

HRID 580160Notes

Reaction equation

HRID 580160 reaction equation
CN(C)C=O.[CH3:6][N:7]([CH3:23])[CH:8]([CH3:22])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([NH2:21])=[N:12]1.Br.Br[CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH3:23][N:7]([CH3:6])[CH:8]([CH3:22])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([NH:21][CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[N:12]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 201357981-(3-Dimethylaminobutyl)-3-amino-5-chloroindazole

Product 1

HCID 201358711-(3-Dimethylaminobutyl)-3-(3-diethylaminopropylamino)-5-chloroindazoleYield 58.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 60 ml of anhydrous N,N-dimethylformamide were added 8.71 g of the 1-(3-dimethylaminobutyl)-3-amino-5-chloroindazole, 8.98 g of 3-bromopropyldiethylamine hydrobromide and 7.89 g of anhydrous potassium carbonate, and the mixture was atirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochloric acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 7.23 g of 1-(3-dimethylaminobutyl)-3-(3-diethylaminopropylamino)-5-chloroindazole having the following analytical values in a yield of 58%.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. extractionThe diethyl ether layer was extracted three times with 2N hydrochloric acid
  4. washthe hydrochloric acid layer was washed with diethyl ether
  5. extractionthe alkali layer was extracted three times with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
  7. customwas removed under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-d402105329914e7299a428b66fd2b1b8
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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