Methylamine → HCID 71294979, compound

HRID 1776905Notes

Reaction equation

HRID 1776905 reaction equation
[Br:1][C:2]1[C:3]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18](O)=[O:19])[C:6]=2[CH:21]=1.C1C=CC2N(O)N=[N:33][C:31]=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.CN>CN(C=O)C>[Br:1][C:2]1[C:3]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18]([NH:33][CH3:31])=[O:19])[C:6]=2[CH:21]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 71295150HCID 71295150, compound

Product 1

HCID 71294979HCID 71294979, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-(2,4-difluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (440 mg, 0.99 mmol), HOBT (199 mg, 1.48 mmol) and EDCI (283 mg, 1.48 mmol) in dry DMF (10 mL) was stirred at 25° C. After 2 hours, Et3N (299 mg, 2.96 mmol) and MeNH2 (200 mg, 2.96 mmol) was added to the mixture and then stirred overnight. The solvent was removed by vacuum, the mixture was washed with H2O (20 mL) and extract with EtOAc (40 mL*3), dried over Na2SO4, After concentrated, the resulting residue was purified using column chromatography (dichloromethane:EtOAc=2:1) to provide 5-bromo-2-(2,4-difluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (400 mg, yield: 88%). 1H-NMR (DMSO-d6, 400 MHz) δ 9.61 (s, 1H), 8.19 (d, J=3.6 Hz, 1H), 7.97 (s, 1H), 7.80˜7.86 (m, 1H), 7.73 (s, 1H), 7.44˜7.50 (m, 1H), 7.27˜7.31 (m, 1H), 3.02 (s, 3H), 2.75 (d, J=4.8 Hz, 3H). MS (M+H)+: 459/461.

Workup

  1. customThe solvent was removed by vacuum
  2. washthe mixture was washed with H2O (20 mL)
  3. extractionextract with EtOAc (40 mL*3)
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrated
  6. customthe resulting residue was purified

Sources & evidence

ORD record
ord-d88c82bba90242d3b1932770e5bd2188
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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