Hydrochloric Acid → HCID 19605495, compound

HRID 1603597Notes

Reaction equation

HRID 1603597 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[C:15]([Br:17])[N:14]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)[CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[C:15]([Br:17])[N:14]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:12]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54175609HCID 54175609, compound

Product 1

HCID 19605495HCID 19605495, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.36 g (0.00072 mol) of tert-butyl [4-[4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-ylamino]-butyl]-carbamate was dissolved in 15 ml of dioxane and treated with 5 ml of 3N aqueous HCl. After stirring at room temperature for 18 hrs. the pH was adjusted to 9, the reaction mixture was extracted with ethyl acetate and the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel with 10% methanol in dichloromethane and then with 20% methanol in dichloromethane. After removal of the solvent from the product-containing fractions the residue was dissolved in diethyl ether and the product was precipitated by the addition of hexane. There was obtained 0.03 g (10%) of N1-[4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-yl]-butane-1,4-diamine as orange-red crystals. MS (ISP): me/e=401, 399 (C15H20BrN4O2S+).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water and sat. sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 10% methanol in dichloromethane
  6. customAfter removal of the solvent from the product-containing fractions the residue
  7. dissolutionwas dissolved in diethyl ether
  8. customthe product was precipitated by the addition of hexane

Sources & evidence

ORD record
ord-061964bbfb9149da8a311e068845cf49
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…