Methanol → HCID 178474087, compound

HRID 1827352Notes

Reaction equation

HRID 1827352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8](OC2CCCCO2)[C:9]([C:11]2[O:12][C:13]3[C:19]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)=[NH:10])[CH:5]=[CH:6][CH:7]=1.C[OH:32]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[O:12][C:13]3[C:19]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)=[N:10][OH:32])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 22137863HCID 22137863, compound

Product 1

HCID 178474087HCID 178474087, compoundYield 73%

Procedure

To a methanol solution of N-{2-[N-(3-chloro-phenyl)-N-(tetrahydro-pyran-2-yloxy)-carbamimidoyl]-benzofuran-7-yl}-acetamide was added 200 mg of acidic Dowex resin. The resulted solution was stirred at reflux temperature for 1 h. The reaction mixture was filtered and concentrated under vacuum. The crude product was purified using a chromatotron and eluting with hexane/ethyl acetate (8:2) to give 25 mg N-{2-[N-(3-chloro-phenyl)-N′-hydroxy-carbamimidoyl]-benzofuran-7-yl}-acetamide in 73% yield.

Workup

  1. temperatureat reflux temperature for 1 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified
  5. washeluting with hexane/ethyl acetate (8:2)

Sources & evidence

ORD record
ord-49f9e940fe6b486a9bf9d23dc5b7136d
Source dataset
uspto-grants-2006_05
Patent number
US07053234B2

Reaction notes

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