Pyridine → HCID 86629777, compound

HRID 2358432Notes

Reaction equation

HRID 2358432 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]([NH:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([I:16])[CH:10]=1)[CH3:8])=[CH2:5].Cl[CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1>C(Cl)Cl>[CH3:18][C:2]([CH3:17])([CH3:1])[CH2:3][C:4]([NH:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:22]([CH:21]=[CH2:20])(=[O:24])=[O:23])=[C:11]([I:16])[CH:10]=1)[CH3:8])=[CH2:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 68456634HCID 68456634, compound

Product 1

HCID 86629777HCID 86629777, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-{1-[1-(2,2-Dimethylpropyl)vinylamino]ethyl}-2-iodophenylamine (218.1 mg, 0.65 mmol) was dissolved in methylene chloride. The reaction mixture was cooled down to 0° C. 2-Chloroethane sulfonyl chloride (3 eq, 1.95 mmol, 203.64 μl) and Pyridine (3 eq, 1.95 mmol, 157.71 μl) were added into mixture. The reaction mixture was stirred for 48 hrs. After confirming the completion of the synthesis, a reaction solvent was removed in vacuo. A residue was extracted with methylene chloride. A combined organic layer was washed with H2O and brine, dried over NaSO4, and concentrated in vacuo. The residue was purified with column chromatography (n-Hx:EA=3:1) to yield title compound (104.9 mg, 78%) as a brownish solid.

Workup

  1. customthe completion of the synthesis
  2. customa reaction solvent was removed in vacuo
  3. extractionA residue was extracted with methylene chloride
  4. washA combined organic layer was washed with H2O and brine
  5. dry with materialdried over NaSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with column chromatography (n-Hx:EA=3:1)

Sources & evidence

ORD record
ord-6e4903c56b6549f2b4122d57aca82501
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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