Triethylamine → 5-bromo-N-methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595600Notes

Reaction equation

HRID 595600 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[O:9][C:10]2[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([Br:27])=[CH:17][C:11]=2[C:12]=1[C:13]([NH:15][CH3:16])=[O:14])=[O:7])(=O)[CH3:2].CCN(CC)CC>C(Cl)Cl>[Br:27][C:18]1[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:23])=[O:24])=[CH:20][C:10]2[O:9][C:8]([C:6]3[O:7][C:1]([CH3:2])=[N:4][N:5]=3)=[C:12]([C:13]([NH:15][CH3:16])=[O:14])[C:11]=2[CH:17]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 903324512-(2-acetylhydrazinecarbonyl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903335625-bromo-N-methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 2-(2-acetylhydrazinecarbonyl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (150 mg, 0.33 mmol), p-TsCl (124 mg, 0.66 mmol) and Et3N (108 mg, 0.98 mmol) in CH2Cl2 (6 mL) was refluxed for 5 h. After concentration in vacuo, the residue was purified with prep-TLC (DCM:MeOH=100:1) to give the product 5-bromo-N-methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (146 mg, yield: 63%). 1H-NMR (CDCl3, 400 MHz) δ 9.80 (br s, 1H), 8.96 (s, 1H), 7.77 (s, 1H), 3.36 (s, 3H), 3.13˜3.06 (m, 6H), 2.75 (s, 3H). MS (M+H)+: 443/445.

Workup

  1. temperaturewas refluxed for 5 h
  2. concentrationAfter concentration in vacuo
  3. customthe residue was purified with prep-TLC (DCM:MeOH=100:1)

Sources & evidence

ORD record
ord-806e21500c204fe3ab0617e9194ee6ee
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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