Methyl iodide → Cyclopropanesulfonic acid methyl-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amide

HRID 83349Notes

Reaction equation

IC.[CH2:3](N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]=1[CH2:28][O:29][C:30]1[N:35]=[CH:34][C:33]([C:36]([NH:38][S:39]([CH:42]2[CH2:44][CH2:43]2)(=[O:41])=[O:40])=[O:37])=[CH:32][CH:31]=1>CN(C=O)C>[CH3:3][N:38]([C:36]([C:33]1[CH:34]=[N:35][C:30]([O:29][CH2:28][C:18]2[C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][C:17]=2[CH3:16])=[CH:31][CH:32]=1)=[O:37])[S:39]([CH:42]1[CH2:44][CH2:43]1)(=[O:40])=[O:41]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of mixture of iodomethane (120 μL, 1.91 mmol), triethylamine (245 μL, 1.75 mmol) and anhydrous sodium carbonate (36.9 mg, 0.35 mmol) in DMF (0.5 mL) was added cyclopropanesulfonic acid [6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amide (44 mg, 0.11 mmol). The reaction mixture was then heated in the microwave for 40 min at 100° C. The mixture was then cooled and evaporated and the residue was purified by chromatography (SiO2, heptane:ethyl acetate 2:1 to 1:1) to give the title compound (3.9 mg, 9%) as a yellow solid. MS: m/e=486.3 [M+OAc]−.

Workup

temperatureThe mixture was then cooled
customevaporated
customthe residue was purified by chromatography (SiO2, heptane:ethyl acetate 2:1 to 1:1)

Sources & evidence

ORD record: ord-5bde3dceba474c248877edd0f95aa30b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846719B2

Reaction notes

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