Ammonia → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine

HRID 548817Notes

Reaction equation

HRID 548817 reaction equation
I[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[NH3:22]>CO.[Cu]Br>[CH3:15][C:14]1[O:13][N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]=1[CH2:9][O:8][C:5]1[N:4]=[N:3][C:2]([NH2:22])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 866308943-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 426297716-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamineYield 46%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolvent

Procedure

3-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (example 15a) (200 mg, 0.5 mmol) was dissolved in a solution of ammonia in methanol (7 M, 3 mL). After addition of copper(I) bromide (88 mg, 0.6 mmol) the mixture was stirred for 16 h at room temperature. The precipitate was filtered and the organic phase was adsorbed on silica. Chromatography (SiO2, dichloromethane:methanol=100:0 to 95:5) afforded the title compound (66 mg, 46%) as a light yellow solid. MS: m/e=283.1 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-94ee8e17ea8a4a90a227dbef2940f33a
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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