Hydrochloric Acid → HCID 18918394, compound

HRID 1291859Notes

Reaction equation

HRID 1291859 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([C:16]3[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:19]([O:20][CH2:21][C:22]([O:24]C)=[O:23])=[C:18]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:17]=3)=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Cl>O1CCOCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]([C:16]3[CH:27]=[C:26]([C:28]([CH3:30])([CH3:29])[CH3:31])[C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[C:18]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:17]=3)=[O:15])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18918233HCID 18918233, compound

Product 1

HCID 18918394HCID 18918394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 4-(2-[4-(4-pyridyl)piperazin-1-yl]-acetyl)-2,6-di-tert-butylphenoxyacetate (241 mg) in dioxane (2.0 ml) was treated with 1N hydrochloric acid and the mixture heated at 100° C. for 20 hours. The mixture was cooled, diluted with water, filtered and the filtrate freeze-dried. The solid residue was purified by flash chromatography on silica eluting with toluene/ethyl acetate/0.880 ammonia/ethanol (60:20:10:35 v/v/v/v). The fractions containing the desired product were evaporated, the residue treated with dioxane, filtered and the filtrate diluted with water and freeze dried to give a white foam, which on drying at 55° C. gave the title compound, 90 mg: NMR (d6DMSO) δ 8.16 (2H, d), 7.97 (2H, s), 6.84 (2H, d), 4.22 (2H, s), 3.86 (2H, s), 3.37 (4H, t), 2.64 (4H, t), 1.39 (18H, s); m/e 468 (M+H)+ ; calculated for C27H37 N3O4.2H2O: C, 64.4; H, 8.2; N, 8.3. found C, 64.6; H, 7.9; N, 7.9%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate freeze-dried
  4. customThe solid residue was purified by flash chromatography on silica eluting with toluene/ethyl acetate/0.880 ammonia/ethanol (60:20:10:35 v/v/v/v)
  5. additionThe fractions containing the desired product
  6. customwere evaporated
  7. additionthe residue treated with dioxane
  8. filtrationfiltered
  9. additionthe filtrate diluted with water and freeze
  10. customdried
  11. customto give a white foam, which
  12. customon drying at 55° C.

Sources & evidence

ORD record
ord-c996f1a0c247449ba6fef5f32f38ffba
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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