tert-butyl N-(4-aminobutyl)carbamate → HCID 54175609, compound

HRID 1603596Notes

Reaction equation

HRID 1603596 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.[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])=[O:25])([CH3:22])([CH3:21])[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:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:26][C:24](=[O:25])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:7]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 54175609HCID 54175609, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

0.39 g (0.001 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane and treated with 1.9 ml (0.01 mol) of N-tert.-butoxycarbonyl-1,4-diaminobutane. The mixture was stirred at 60° C. for 18 hrs., the solvent was removed and the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. There was obtained 0.36 g (77%) of tert-butyl [4-[4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-ylamino]-butyl]-carbamate as a pale yellow oil. MS (ISP): me/e=501, 499 (C20H26BrN4O4S+).

Workup

  1. custom, the solvent was removed
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-1c81f32f3ec54f10a8ad69290fba298a
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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