O-Methylhydroxylamine hydrochloride → HCID 86590419, compound

HRID 2214079Notes

Reaction equation

HRID 2214079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][C:24]2=O)[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].Cl.[CH3:30][O:31][NH2:32]>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[N:32][O:31][CH3:30])[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 21959027HCID 21959027, compound

Product 1

HCID 86590419HCID 86590419, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide (prepared as in Example 32, 99.5 mg, 0.23 mmol) in pyridine (0.69 mL) and methanol (0.69 mL) at 25° C. was treated with methoxyamine hydrochloride (30 mg, 0.35 mmol). The reaction mixture was heated under reflux for 12 h. At this time, the reaction was cooled to 25° C. and was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (75 mL) and was washed with a 1N aqueous sodium hydroxide solution (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 75/25 ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(2-methoxyimino-cyclopentyl)-N-pyrazin-2-yl-propionamide (92.7 mg, 87.2%) as a white wax: mp 74–76° C.; FAB-HRMS m/e calcd for C20H23ClN4O4S (M+Na)+ 473.1021, found 473.1024.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in ethyl acetate (75 mL)
  5. washwas washed with a 1N aqueous sodium hydroxide solution (1×50 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8514de485704d5f8f71f4d6ab23e42d
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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