Isopropylamine → 3-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropyl-amide

HRID 1920909Notes

Reaction equation

CO[C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[CH:24]([NH2:27])([CH3:26])[CH3:25].N12CCCNC1=NCCC2>C1(C)C=CC=CC=1>[CH:24]([NH:27][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol) and isopropyl amine (22 mg, 0.37 mmol) in toluene (1 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (26 mg, 0.19 mmol) and the reaction stirred under argon for 3 h at 50° C. Then the mixture was evaporated and the residue purified by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) to afford the title compound (95 mg, 83%) which was obtained as an off-white solid. MS: m/e=343.2 [M+H]+.

Workup

customThen the mixture was evaporated
customthe residue purified by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record: ord-b8d237266f524e74a495cdd45338b4bb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173652B2

Reaction notes

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