4-Fluorophenyl isocyanate → 2-[3-(4-Fluorophenyl)ureido]-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45370

Reaktionsgleichung

Reaktionsgleichung von HRID 45370
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH2:26])=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH:26][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:10])=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 709554-Fluorophenyl isocyanateHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Produkt 1

HCID 168977312-[3-(4-Fluorophenyl)ureido]-4-methylthiazole-5-carboxylic Acid BenzylamideAusbeute 83 %

Versuchsvorschrift

Following the procedure as described in Example 4, making variations only as required to use 4-fluorophenyl isocyanate in place of phenyl isocyanate to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 83% yield; m.p.>300° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.03 (s, 1H), 8.47 (t, J=6.0 Hz, 1H), 7.49-7.05 (m, 10H), 4.35 (d, J=5.7 Hz, 2H), 2.43 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 162.2, 140.2, 128.7, 127.7, 127.2, 121.1, 121.0, 120.5, 116.1, 115.9, 115.8, 43.0, 39.1; MS (ES+) m/z 385.1 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-7b22915512bc47979126fd0a94fbfa22
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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