Isopropylamine → 3-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid isopropyl-amide
Reaction equation
CO[C:3]([C:5]1[S: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].COC(C1ON=C(OC[C:35]2[C:36]([C:41]3C=CC=CN=3)=[N:37]OC=2C)C=1)=O.C(N)(C)C>>[CH:36]([NH:37][C:3]([C:5]1[S: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])([CH3:41])[CH3:35]Participants
4
Reactant 3
Product 1
Procedure
As described for example 14e, 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol), instead of 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester, was converted, using isopropyl amine (22 mg, 0.37 mmol), to the title compound (95 mg, 83%) which was obtained as an off white solid after purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:4). MS: m/e=343.2 [M+H]+.
Sources & evidence
- ORD record
- ord-e6091cc6f6994919817ce4dda1853962
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173652B2
Reaction notes
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