N,N-Diethyl-1,3-propanediamine → HCID 19605488, compound

HRID 1603594Notes

Reaction equation

HRID 1603594 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][CH2:24][NH2:25])[CH3:20]>O1CCOCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([Br:18])[N:3]=[C:2]([NH:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH3:27])[CH2:19][CH3:20])[CH:7]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 19605488HCID 19605488, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.20 g (0.00051 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane and treated with 8.0 ml of 3-diethylamino-1propylamine. The mixture was stirred at room temperature for 18 hrs., the solvent was removed and the residue was chromatographed twice on silica gel, firstly with 20% methanol in dichloromethane and then with 10% methanol in dichloromethane. There was obtained 0.09 g (41%) of N-[4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-yl]-N',N'-diethylpropane-1,3-diamine as a pale yellow, amorphous solid. MS (ISP): me/e=443, 441 (C18H26BrN4O2S+).

Workup

  1. custom, the solvent was removed
  2. customthe residue was chromatographed twice on silica gel, firstly with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-2d479d3f93ae4f7da8e020742e5dec5c
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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