HCID 69688057, compound → HCID 22396304, compound

HRID 1070413Notes

Reaction equation

HRID 1070413 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14]([CH2:16][O:17][C:18](=[O:30])[NH:19][C:20]4[C:28]5[C:27](=[O:29])[O:26][NH:25][C:24]=5[CH:23]=[CH:22][CH:21]=4)=[CH:13][C:12]=3[CH:31]=2)=[CH:4][CH:3]=1>OS(O)(=O)=O.[Zn]>[NH2:25][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:19][C:18]([O:17][CH2:16][C:14]2[O:15][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:31][C:12]=3[CH:13]=2)=[O:30])[C:28]=1[C:27]([OH:29])=[O:26]

Participants

4

Reactant 1

HCID 69688057HCID 69688057, compound

Product 1

HCID 22396304HCID 22396304, compoundYield 32.86%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

(3-Oxo-1,3-dihydrobenzo[c]isoxazol-4-yl)carbamic acid 5-(4-fluorophenyl)benzofuran-2-ylmethyl ester (70 mg, 0.17 mmol) was dissolved in 2M H2SO4 at room temperature. Zinc dust was added and the mixture was stirred at 80° C. for 4 hours. Upon cooling, the mixture was filtered. The filtrate was neutralized with diluted NaOH and extracted with CH2Cl2. The organic extracts were dried over anhydrous Na2SO4 and concentrated en vacuo to give 23 mg (32.86%) of 2-amino-6-[5-(4-fluorophenyl)benzofuran-2-ylmethoxycarbonylamino]benzoic acid 701, as a tan powder: mp: 176.4-178.5° C. Anal Calcd for C23H17FN2O5: C, 65.71; H, 4.08; N, 6.66. Found: C, 66.71; H, 4.56; N, 5.95.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated en vacuo

Sources & evidence

ORD record
ord-4e6044ff1ea242eba22ffc8cdb7214fa
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

Loading…