Triethylamine → N-[2-Acetyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]-N-(methylsulfonyl)methanesulfonamide

HRID 8784Notes

Reaction equation

HRID 8784 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26](=[O:28])[CH3:27].[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[C:26]([C:3]1[O:4][C:5]2=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=[C:10]2[C:2]=1[N:1]([S:30]([CH3:29])(=[O:32])=[O:31])[S:30]([CH3:29])(=[O:32])=[O:31])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 104105121-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

Product 1

HCID 10348361N-[2-Acetyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]-N-(methylsulfonyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.030 g (0.0696 mmol)of the product from Example 5 in CH2Cl2 (1 mL) cooled to 0° C. was treated with methanesulfonyl chloride (5 μL; 0.0696 mmol), followed by triethylamine (30 μL; 0.209 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 586.9 (M+1), 588.9 (M+3); Rt=4.16 min.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  3. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Sources & evidence

ORD record
ord-8c635e54935543898c0a9c00395ecef1
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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