Triethylamine → HCID 90462314, compound

HRID 588793Notes

Reaction equation

HRID 588793 reaction equation
[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][NH2:16])[CH:10]=[CH:9][N:8]=2)=[C:4]([I:20])[CH:3]=1.CCN(CC)CC.Cl[CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][NH:16][S:31]([CH:30]=[CH2:29])(=[O:33])=[O:32])[CH:10]=[CH:9][N:8]=2)=[C:4]([I:20])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 117607155HCID 117607155, compound

Product 1

HCID 90462314HCID 90462314, compoundYield 155.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(2-(4,5-dichloro-2-iodophenoxy)pyridin-4-yloxy)ethanamine (30 mg, 0.07 mmol), Et3N (35.7 mg, 0.35 mmol) in DCM (5 mL), 2-chloroethanesulfonyl chloride (11.5 mg, 0.07 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. Then solvent was removed under reduced pressure. The residue was taken in THF (2 mL) and H2O (2 mL), then K2CO3 (100 mg) was added and the resulting mixture was stirred at room temperature for 1 h. The mixture was partitioned between DCM and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/ethyl acetate=5:1) to afford the desired product (56 mg, 56% yield). 1H NMR (400 MHz, CDCl3) δ: 7.98 (d, J=5.6 Hz, 1H), 7.92 (s, 1H), 7.25 (s, 1H), 6.61-6.57 (m, 2H), 6.47 (d, J=2.0 Hz, 1H), 6.32 (d, J=16.4 Hz, 1H), 6.00 (d, J=10.0 Hz, 1H), 4.77 (t, J=5.2 Hz, 1H), 4.18 (t, J=5.2 Hz, 2H), 3.51-3.47 (m, 2H). ESI-MS m/z: 515.0[M+H]+.

Workup

  1. additionwas added
  2. customThen solvent was removed under reduced pressure
  3. additionH2O (2 mL), then K2CO3 (100 mg) was added
  4. stirringthe resulting mixture was stirred at room temperature for 1 h
  5. customThe mixture was partitioned between DCM and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography on silica gel (DCM/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-abed541efc794d8bb25024a98c7448f8
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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