Hydrochloric Acid → HCID 178487389, compound

HRID 2409995Notes

Reaction equation

HRID 2409995 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]#[C:26][C:27](OC)=[O:28])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[NH2:31][OH:32].[OH-].[Na+].Cl>CO.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]4[O:32][N:31]=[C:27]([OH:28])[CH:26]=4)[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 86703299HCID 86703299, compound

Product 1

HCID 178487389HCID 178487389, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl [6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridin-2-yl]propynoate (73 mg) and hydroxylamine (50% aqueous solution, 18.2 mg) in methanol (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.166 mL), and this mixture was stirred at room temperature for 64 hours. To the reaction mixture were added water, ethyl acetate, and 2 mol/L hydrochloric acid (0.230 mL). The organic layer was separated. This organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (33 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.34 (2H, s), 6.51 (1H, s), 6.60-6.68 (1H, m), 6.87 (1H, d, J=2.3 Hz), 7.24-7.43 (3H, m), 7.44-7.54 (2H, m), 7.64-7.73 (1H, m), 7.76-7.87 (3H, m), 11.16 (1H, s), 11.47 (1H, s).

Workup

  1. customThe organic layer was separated
  2. washThis organic layer was washed with water and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c17fcc6d2ad64f9d8f37f0a9000bff2e
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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