2-Amino-thiazole-5-carboxylic acid ethyl ester → (E)-ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylate
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19](/[C:22](=[CH:26]\[CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)/[C:23](O)=[O:24])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>>[CH3:12][S:13]([C:16]1[CH:17]=[CH:18][C:19](/[C:22](=[CH:26]\[CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)/[C:23]([NH:1][C:2]2[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=2)=[O:24])=[CH:20][CH:21]=1)(=[O:15])=[O:14]Participants
Procedure
Ethyl 2-aminothiazole-5-carboxylate (0.73 g, 4.26 mmol) was condensed with (E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid (Preparation 25, 0.33 g, 1.07 mmol), using the procedure described in EXAMPLE 65, to give (E)-ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylate: m/z (ES+)=465.3 [M+H]+. This ester (0.50 g, 1.07 mmol) was saponified, employing the protocol described in EXAMPLE 127, to furnish (E)-2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES−)=435.2 [M−H]−. Utilising the approach described in EXAMPLE 129, this acid (0.16 g, 0.37 mmol) was transformed into the title compound: RTA=2.87 min; m/z (ES+)=450.2 [M+H]+.
Sources & evidence
- ORD record
- ord-3ee2a02672654e138d63405286c9e57d
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214681B2
Reaction notes
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