O-Methylhydroxylamine hydrochloride → HCID 54097458, compound

HRID 381985Notes

Reaction equation

HRID 381985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:17][C:18](=O)[CH3:19])=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.[CH3:32][O:33][NH2:34].O.O.O.C([O-])(=O)C.[Na+]>O.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:17][C:18](=[N:34][O:33][CH3:32])[CH3:19])=[C:12]([C:21]3[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][CH:26]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 21934046HCID 21934046, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 54097458HCID 54097458, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(3,4-difluorophenyl)-4-(2-oxo-1-propoxy)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone from Example 460 (150 mg, 0.3 mmol) in H2O (10 mL) and dioxane (20 mL) was treated with methoxyamine hydrochloride (84 mg, 1 mmol) and sodium acetate trihydrate (138 mg, 1 mmol). The mixture was stirred at room temperature for 6 hours. The reaction mixture was extracted with ethyl acetate and purified by column chromatography (silica gel, 1:1 hexanes-ethyl acetate) to provide the title compound (yield: 20 mg, 15%). mp 143-145° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.63 (s, 3H), 3.30 (s, 3H), 3.74 (s, 3H), 4.93 (s, 2H), 7.54 (m, 1H), 7.65 (q, J=10 Hz, 1H), 7.82 (m, 1H), 7.92 (d, J=9 Hz, 2H), 8.07 (d, J=9 Hz, 2H), 8.24 (s, 1H); MS (APCI+) m/z 464 (M+H)+; (APCI−) m/z 498 (M+Cl)−. Anal. calc. for C21H19F2N3OS: C, 54.42; H, 4.13; N, 9.06. Found: C, 54.33; H, 3.93; N, 8.92.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. custompurified by column chromatography (silica gel, 1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-b3fd15894d094833ae5c3711f19fba4d
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

Loading…