Ammonia → HCID 11662698, compound

HRID 2059607Notes

Reaction equation

HRID 2059607 reaction equation
C(O[C:4](=[O:36])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[O:12][C:13]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:14]=3[C:15]=2[C:16](=[O:29])[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH:8]=[N:7]1)C.[NH3:37]>>[CH3:35][O:34][C:32]1[CH:31]=[CH:30][C:14]2[C:15]([C:16](=[O:29])[C:17]3[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=3)=[C:11]([C:9]3[CH:8]=[N:7][N:6]([CH2:5][C:4]([NH2:37])=[O:36])[CH:10]=3)[O:12][C:13]=2[CH:33]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11720177HCID 11720177, compound

Product 1

HCID 11662698HCID 11662698, compoundYield 14%

Conditions

Temperature
80 °C

Procedure

{4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester (30 mg, 0.061 mmol) was treated with 28% aqueous ammonia solution and the resulting reaction mixture was stirred at 80° C. for 3 h. After cooling to room temperature the solution was concentrated under vacuum and the residue subjected to flash column chromatography (silica gel, sequential elution—1:1 hexane:ethyl acetate, ethyl acetate). The resulting product was further purified by trituration with 1:1 hexane:diethyl ether to give the title compound as a yellow solid (4 mg, 14%). 1H-NMR (CDCl3) δ 8.29 (s, 1H), 8.14 (s, 1H), 7.13 (s, 2H), 7.12 (d, J=8.7 Hz, 1H), 7.05 (d, J=2.1 Hz, 1H), 6.81 (dd, J=8.7, 2.1 Hz, 1H), 6.14 (br s, N—H), 5.46 (br s, N—H), 4.83 (s, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.78 (s, 6H).

Workup

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling to room temperature the solution
  3. concentrationwas concentrated under vacuum
  4. customThe resulting product was further purified by trituration with 1:1 hexane

Sources & evidence

ORD record
ord-6b3d2a981a4a492db0c1716acee572a8
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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