(2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid → HCID 86758670, 화합물

반응식

[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=1[CH3:8].Br[CH:15]([CH3:29])[C:16]([C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([F:28])[CH:19]=1)=O.FC1C=C(C2N=C(C3C(C)=C(C(OC)=S)SC=3)SC=2C)C=C(C(F)(F)F)C=1.C1C(/C=C(/C(O)=O)\C#N)=CC=C(O)C=1>>[F:28][C:20]1[CH:19]=[C:18]([C:16]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=3[CH3:8])[S:13][C:15]=2[CH3:29])[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=1

참가 물질

반응물 4

HCID 5328791(2E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid

HCID 18537339HCID 18537339, 화합물

HCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

HCID 86758671HCID 86758671, 화합물

생성물 1

HCID 86758670HCID 86758670, 화합물

실험 절차

A solution of 75 mg (0.3 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge, Cornwall, UK) was reacted with 90 mg (0.3 mmol) of 2-bromo-1-[3-fluoro-5-(trifluoromethyl)phenyl]propan-1-one in a manner similar to Example 8, step (a) to give, methyl 4-{4-[3-fluoro-5-(trifluoromethyl)phenyl]-5-methyl(1,3-thiazol-2-yl)}-methylthiothiophene-2-carboxylate (31.9 mg, 24%) as a solid. 1H-NMR (DMSO-d6; 300 MHz) δ8.17 (s, 1H), 7.98 (m, 1H), 7.95 and 7.92 (m, 1H, 1:1 ratio conformers), 7.77 and 7.74 (m, 1H, 1:1 ratio conformers), 3.87 (s, 3H), 2.75 (s, 3H), 2.70 (s, 3H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C18H13NO2S3F4, 448.0 (M+H), found 448.0.