Pyrrolidine → HCID 19605470, compound

HRID 1603563Notes

Reaction equation

HRID 1603563 reaction equation
I[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]([I:18])[N:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[I:18][C:4]1[CH:5]=[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:7]=[C:2]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 19605447HCID 19605447, compound

Product 1

HCID 19605470HCID 19605470, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.127 g (0.000261 Mol) 4-(2,6-Diiodo-pyridine-4-sulfonyl)-phenylamine were dissolved in dioxane (5 ml) and treated with 0.22 ml (0.0026 Mol) pyrrolidine for 6 h at ambiente temperature. Then the solvent was removed, the residue dissolved in ethyl acetate, washed with 1N HCl, sat. bicarbonate and brine, dried over MgSO4 and evaporated. After chromatography on SiO2 with ethyl acetate hexane 1:2 and drying in a high vacuum it was obtained 0.084 g (75%) of 4-(2-iodo-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine as a beige solid; mp.: 218-221° C. (dec.).

Workup

  1. customThen the solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with 1N HCl, sat. bicarbonate and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. dry with materialAfter chromatography on SiO2 with ethyl acetate hexane 1:2 and drying in a high vacuum it

Sources & evidence

ORD record
ord-edb9709b73e2405098421727b32f2629
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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