4-Aminotetrahydropyran → HCID 46897362, compound

HRID 1920948Notes

Reaction equation

CO[C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:6]=1)=[O:4].[NH2:26][CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[O:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:3]([C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]3[C:13]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[N:14][O:15][C:16]=3[CH2:17][OH:18])[CH:6]=2)=[O:4])[CH2:28][CH2:29]1

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 67492207HCID 67492207, compound

Product 1

HCID 46897362HCID 46897362, compoundYield 46%

Procedure

As described for example 43 g, 3-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.29 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (55 mg, 46%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol=1:0 to 9:1). MS: m/e=416.1 [M−H]−.

Sources & evidence

ORD record: ord-a583293f6ae44c88940a3f759ae5f51f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173652B2

Reaction notes

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