Acetic Acid → 2-(2-acetylhydrazinecarbonyl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595599Notes

Reaction equation

HRID 595599 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]([NH:12][NH2:13])=[O:11])=[C:7]([C:14]([NH:16][CH3:17])=[O:15])[C:6]=2[CH:18]=1.CCN=C=NCCCN(C)C.[C:36](O)(=[O:38])[CH3:37]>CN(C=O)C>[C:36]([NH:13][NH:12][C:10]([C:8]1[O:9][C:5]2[CH:4]=[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:21])=[O:22])[C:2]([Br:1])=[CH:18][C:6]=2[C:7]=1[C:14]([NH:16][CH3:17])=[O:15])=[O:11])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 903325365-bromo-2-(hydrazinecarbonyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903324512-(2-acetylhydrazinecarbonyl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 5-bromo-2-(hydrazinecarbonyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (210 mg, 0.50 mmol), EDCI (384 mg, 2.0 mmol) and acetic acid (60 mg, 1.0 mmol) in DMF (5 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, the residue diluted with water, and the resulting solid was filtered to give the product 2-(2-acetylhydrazinecarbonyl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (146 mg, yield: 63%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.25 (br s, 1H), 10.22 (s, 1H), 9.68 (br s, 1H), 8.52 (s, 1H), 8.02 (s, 1H), 3.20 (s, 3H), 3.17 (s, 3H), 2.83 (d, J=4.4 Hz, 3H), 1.92 (s, 2H). MS (M+H)+: 461/463.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue diluted with water
  3. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-6e8c1672e5dc4e92a04b61db5ce3812d
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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