Methanol → HCID 178507401, compound

HRID 858319Notes

Reaction equation

HRID 858319 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:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]=2O)=[NH:10])[CH:5]=[CH:6][CH:7]=1.C[OH:30]>>[NH2:21][C:20]1[C:13]2[O:12][C:11]([C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:10][OH:30])=[CH:15][C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 135830899HCID 135830899, compound

Product 1

HCID 178507401HCID 178507401, compoundYield 62%

Procedure

To a methanol solution of 32 mg of N-(3-chloro-phenyl)-hydroxy-7-amino-N-(tetrahydro-pyran-2-yloxy)-benzofuran-2-carboxamidine was 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 5–10% methanol/dichloromethane to give 18 mg of 7-amino-N-(3-chloro-phenyl)-N′-hydroxy-benzofuran-2-carboxamidine in 62% 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 5–10% methanol/dichloromethane

Sources & evidence

ORD record
ord-e2d502016e2e4752b5b4918db9a39f6f
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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