Azetidine → Azetidin-1-yl-[6-((3-butyl-5-methyl-isoxazol-4-yl)methoxy)-pyridin-3-yl]-methanone

HRID 1807508Notes

Reaction equation

HRID 1807508 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[NH:22]1[CH2:25][CH2:24][CH2:23]1>>[N:22]1([C:16]([C:15]2[CH:14]=[N:13][C:12]([O:11][CH2:10][C:9]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=3[CH3:21])=[CH:20][CH:19]=2)=[O:18])[CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 49801023Azetidin-1-yl-[6-((3-butyl-5-methyl-isoxazol-4-yl)methoxy)-pyridin-3-yl]-methanoneYield 39%

Procedure

As described for example 19b, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) was converted, using azetidine instead of L-2,2,2-trifluoro-1-(methyl)ethylamine, to the title compound (45 mg, 39%) which was obtained as a light yellow oil after purification by chromatography (silica, heptane:ethyl acetate=1:0 to 2:1). MS: m/e=330.3 [M+H]+.

Sources & evidence

ORD record
ord-ab13ee805b79495e92170033f3361d69
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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