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

HRID 1923546Notes

Reaction equation

HRID 1923546 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][CH2:11][C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[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:18]([C:14]2[S:13][C:12]([CH2:11][CH2:10][C:9]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=3[CH3:21])=[N:16][C:15]=2[CH3:17])=[O:20])[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 666436692-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 497820402-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (tetra-hydro-pyran-4-yl)-amideYield 60%

Procedure

As described for example 48e, 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (75 mg, 0.23 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (55 mg, 60%) which was obtained as a light brown oil. MS: m/e=392.1 [M+H]+.

Sources & evidence

ORD record
ord-3c1e4621180b44d6a1c91f1bee18cde7
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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