Dimethylformamide → 1,3-Propanediamine,n3-(4-chloro-1h-indazol-3-yl)-n1,n1-diethyl-

HRID 484852Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:11])[NH:4][N:3]=1.Br.Br[CH2:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(Cl)(Cl)Cl.O>[CH2:18]([N:17]([CH2:20][CH3:21])[CH2:16][CH2:15][CH2:14][NH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:11])[NH:4][N:3]=1)[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture consisting of 5.04 g of 3-amino-4-chloroindazole, 8.30 g of 3-bromopropyldiethylamine hydrobromide, 8.3 g of anhydrous potassium carbonate and 80 ml of anhydrous N,N-dimethylformamide was stirred for 24 hours at 80° C. The reaction mixture was condensed under reduced pressure, the condensed residue was added with 100 ml of chloroform and 50 ml of water. The chloroform layer was separated and dried over anhydrous sodium sulfate, and then 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 5.16 g of 3-(3-diethylaminopropylamino)-4-chloroindazole having the following analytical values in a yield of 61%.

Workup

customcondensed under reduced pressure
customThe chloroform layer was separated
dry with materialdried over anhydrous sodium sulfate
customchloroform was removed under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-bbc14edc87a24977b34d5b8dc80faa80
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04533731

Reaction notes

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