Hydroxylamine HCl → HCID 86703291, compound

HRID 2409977Notes

Reaction equation

HRID 2409977 reaction equation
[Cl-].[OH:2][NH3+:3].C(=O)([O-])O.[Na+].[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH2:26][C:27]3[N:32]=[C:31]([C:33](OC)=[O:34])[CH:30]=[CH:29][CH:28]=3)=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17]2)=[CH:13][CH:12]=1>CS(C)=O.O>[OH:2][NH:3][C:33]([C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:26][C:15]2[C:14]3[C:18](=[CH:19][C:11]([O:10][CH3:9])=[CH:12][CH:13]=3)[NH:17][C:16]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:32]=1)=[O:34]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 50903302HCID 50903302, compound

Product 1

HCID 86703291HCID 86703291, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of hydroxylammonium chloride (373 mg) in dimethylsulfoxide (2.7 mL) was added sodium hydrogen carbonate (541 mg), and this mixture was stirred at 50° C. for 70 minutes. Then, methyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (200 mg) was added thereto, followed by stirring at 50° C. for 3 days. The reaction mixture was left to be cooled and diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (186 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.38 (2H, s), 6.63 (1H, dd, J=2.3, 8.5 Hz), 6.87 (1H, d, J=2.3 Hz), 7.15 (1H, dd, J=1.5, 7.3 Hz), 7.29-7.39 (2H, m), 7.42-7.53 (2H, m), 7.59-7.70 (2H, m), 7.70-7.81 (2H, m), 9.13 (1H, s), 11.10 (1H, s), 11.18 (1H, s). ESI-MS (m/z): 374 (M+H)+

Workup

  1. stirringby stirring at 50° C. for 3 days
  2. waitThe reaction mixture was left
  3. temperatureto be cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-a91a0119c9d848c9b2a83ebce4308659
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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