3,6-Dichloropyridazine → (6-Chloro-pyridazin-3-yl)-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amine

HRID 548881Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][NH2:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[Cl:16][C:17]1[N:18]=[N:19][C:20]([NH:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:15])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of C-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methylamine (206 mg, 1.0 mmol) and 3,6-dichloropyridazine (149 mg, 1.0 mmol) in DMSO (2 mL) containing N,N-diisopropyl ethyl amine (259 mg, 342 μL, 2.0 mmol) was heated with microwave irradiation to 160° C. for 1 h. After cooling to room temperature the reaction mixture was extracted (ethyl acetate/water). The organic phase was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (99 mg, 31%) as an off white solid after recrystallization from heptane:ethyl acetate. MS: m/e=319.1 [M+H]−.

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionwas extracted (ethyl acetate/water)
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated
customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record: ord-302abb9bc4fa49778364baa14d174bef
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943619B2

Reaction notes

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