Dimethylformamide → 1,3-Propanediamine, N,N-diethyl-N'-(1H-indazol-3-yi)-

HRID 580131Notes

Reaction equation

CN(C)C=O.[NH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1.Br.Br[CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[CH2:22]([N:21]([CH2:24][CH3:25])[CH2:20][CH2:19][CH2:18][NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To 80 ml of anhydrous N,N-dimethylformamide were added 4 g of 3-aminoindazole as prepared in accordance with the method described in C. E. Kwartler et al., J. Am. Chem. Soc., 65, 1804 (1943), 8.3 g of 3-bromopropyldiethylamine hydrobromide and 8.3 g of anhydrous potassium carbonate. The mixture was stirred for 24 hours at 80° C. and condensed under reduced pressure. To the condensed residue were added 100 ml of chloroform and 50 ml of water. 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 3.85 g of 3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 52%.

Workup

customas prepared in accordance with the method
customcondensed under reduced pressure
dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
customwas removed under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-83b33f51523541bf852c87362a033069
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751302

Reaction notes

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