Ethanol → 3-(2-Amino-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide

HRID 1642336Notes

Reaction equation

HRID 1642336 reaction equation
[CH3:1][C:2]([NH:10][C:11]([C:13]1[O:20][C:19]2[C:18]([NH:21][C:22](=[O:32])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:29]([O-])=O)=[N:17][NH:16][C:15]=2[CH:14]=1)=[O:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].C(O)C>>[CH3:3][C:2]([NH:10][C:11]([C:13]1[O:20][C:19]2[C:18]([NH:21][C:22](=[O:32])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH2:29])=[N:17][NH:16][C:15]=2[CH:14]=1)=[O:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

3

Reactant 2

HCID 702EthanolHCID 578786433-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide

Product 1

HCID 578786473-(2-Amino-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amideYield 59.3%

Procedure

To a solution of 3-(2-Nitro-benzoylamino)-1H-furo[3,2-c]pyrazole-5-carboxylic acid (1-methyl-1-phenyl-ethyl)-amide (1 g, 0.0023 mol) in ethanol (30 mL) tin chloride dihydrate (2.08 g, 0.00923 mol) was added. The mixture was heated to reflux for 4 hours. After cooling, the solvent was evaporated to dryness and the crude purified by flash column chromatography on silica gel (eluting with dichloromethane-methanol 4713. The isolated product was triturated with ethyl ether and dry under vacuum, furnishing 550 mg of the title compound (59% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated to dryness
  5. customthe crude purified by flash column chromatography on silica gel (
  6. washeluting with dichloromethane-methanol 4713
  7. customThe isolated product was triturated with ethyl ether
  8. customdry under vacuum

Sources & evidence

ORD record
ord-8fe34bce253f4bc391df4751e8d279b4
Source dataset
uspto-grants-2012_02
Patent number
US08119641B2

Reaction notes

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