4-Aminotetrahydropyran → 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 1923556Notes

Reaction equation

CO[C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][CH:6]=1)=[O:4].[NH2:22][CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[O:26]1[CH2:27][CH2:28][CH:23]([NH:22][C:3]([C:5]2[S:9][C:8]([CH2:10][CH2:11][C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])=[N:7][CH:6]=2)=[O:4])[CH2:24][CH2:25]1

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 66643644HCID 66643644, compound

Product 1

HCID 497822762-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 76%

Procedure

As described for example 57b, 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid methyl ester (90 mg, 0.29 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (50 mg, 76%) which was obtained as a light yellow solid. MS: m/e=378.4 [M+H]+.

Sources & evidence

ORD record: ord-1df04a6489934393b379fb8df6d0c7c0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178522B2

Reaction notes

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