Methylamine → HCID 90332526, compound

HRID 595582Notes

Reaction equation

HRID 595582 reaction equation
[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH2:14][CH2:13][CH2:12][CH:11]=3)=[C:7]([C:15](O)=[O:16])[C:6]=2[CH:18]=1.C1C=CC2N(O)N=[N:31][C:29]=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.CN>CN(C=O)C>[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH2:14][CH2:13][CH2:12][CH:11]=3)=[C:7]([C:15]([NH:31][CH3:29])=[O:16])[C:6]=2[CH:18]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 90332445HCID 90332445, compound

Product 1

HCID 90332526HCID 90332526, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-(cyclopent-1-en-1-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxylic acid (3.5 g, 7.70 mmol), HOBT (1.6 g, 11.55 mmol) and EDCI (2.2 g, 11.55 mmol) in dry DMF (40 mL) was stirred at 25° C. After 2 hours, Et3N (2.4 g, 23.11 mmol) and MeNH2 (1.6 g, 23.11 mmol) were added to the mixture and then stirred overnight. The solvent was removed by vacuum, the mixture was washed with H2O (50 mL) and extracted with EtOAc (50 mL*3), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (DCM) to give the product of 5-bromo-2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (2 g, yield: 56%). 1H-NMR (CDCl3, 400 MHz) δ 8.00 (s, 1H), 7.59 (s, 1H), 6.70 (t, J=3.2 Hz, 1H), 5.95 (s, 1H), 3.31 (s, 3H), 3.30 (s, 3H), 3.06 (s, 3H), 2.76˜2.81 (m, 2H), 2.58˜2.62 (m, 2H), 2.07 (t, J=7.6 Hz, 2H). MS (M+H)+: 427/429.

Workup

  1. customThe solvent was removed by vacuum
  2. washthe mixture was washed with H2O (50 mL)
  3. extractionextracted with EtOAc (50 mL*3)
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by column chromatography (DCM)

Sources & evidence

ORD record
ord-fa00be474d8e45c0b84e14fa04f9f928
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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