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Methylamine → HCID 67393824, compound

HRID 1776939
Notes
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Reaction equation

HRID 1776939 reaction equation
[Br:1][C:2]1[C:3]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17](O)=[O:18])[C:6]=2[CH:20]=1.C1C=CC2N(O)N=[N:32][C:30]=2C=1.CCN=C=NCCCN(C)C.CN>CN(C=O)C.CCN(CC)CC>[Br:1][C:2]1[C:3]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([NH:32][CH3:30])=[O:18])[C:6]=2[CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67393208HCID 67393208, compound

Product 1

HCID 67393824HCID 67393824, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8471TriethylamineSolvent

Procedure

A solution of 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (33 g, 77 mmol), HOBT (15.6 g, 115.5 mmol) and EDCI (22.2 g, 115.5 mmol) in DMF (250 mL) was stirred at room temperature. After 2 hours, Et3N (50 mL) and CH3NH2 (HCl salt, 17.7 g, 231 mmol) was added to the mixture, and the mixture was stirred overnight. After the solvent was removed, H2O was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with H2O, brine and concentrated in vacuo. The resulting residue was washed with EtOAc to provide the product of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (32 g, yield: 94%). 1H-NMR (DMSO-d6, 400 MHz) δ 9.55 (br s, 1H), 8.46˜8.48 (m, 1H), 8.12˜8.17 (m, 2H), 7.96 (s, 1H), 7.87 (s, 1H), 7.45˜7.50 (m, 2H), 3.16 (s, 3H), 2.93 (d, J=8.4 Hz, 3H). MS (M+H)+: 441/443.

Workup

  1. customAfter the solvent was removed
  2. additionH2O was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layer was washed with H2O, brine
  5. concentrationconcentrated in vacuo
  6. washThe resulting residue was washed with EtOAc

Sources & evidence

ORD record
ord-447030579d5c459cafe849dcdd7b8e58
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265773B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes