4-(4-Pyridinyl)-2(3H)-thiazolethione

Pale yellow powder

In 1000 ml water, adding 60 g 4-acetylpyridine, 10-15 °C lower, added after hydrobromic acid 101 g 40percent, gradually dropping 87.9 g bromine, after dripping 10-15 °C reaction under 1 hour, heating to 30-35 °C reaction 4 hours, HPLC detection raw material after the reaction is complete, cooling to 0 °C, by adding 66 g dithio ammonium dithiocarbamate, after adding 0 °C reaction 1 hour, then heating to 20-25 °C reaction 4 hours, filtering, to obtain 2-mercapto-4-pyridyl thiazole crude 81.7 g, crude product reflux in water for 2 hours, filtered to get after cooling to 2-mercapto-4-pyridylthiazole 80.2 g, yield 82.6percent as a pale yellow solid, HPLC purity was 99.7percent.2.2 908 g (4.6 mol) of Take 24.2g 3-chloro cephalosporin and 7.8g 4- (4-pyridyl) -2-mercapto thiazole dissolved in 200ml carbon tetrachloride, protected by nitrogen, under light conditions, slowly added 0.58g t-butyl hydroperoxide, stir After 30 minutes, the program was warmed to 88 ° C and the reaction mixture was stirred until the peak area of 3-chlorocepam was less than 0.2percent in HPLC.The reaction mixture was transferred to a rotary evaporator vacuum decompression 1/2 volume of solvent, the reaction solution was slowly cooled to 0 ° C, crystallization overnight; suction filtration, the filter cake was rinsed with 400ml of n-hexane, and dried;(7-phenylacetamido-3- [4- (1-methyl-4-pyridyl) -2-thiazolylthio] -3-cephem-4-carboxylic acidDiphenylmethyl ester hydrochloride) 31.1 g, molar yield 97.1percent.In 1000 ml water, adding 60 g 4-acetylpyridine, 10-15 °C lower, added after hydrobromic acid 101 g 40percent, gradually dropping 87.9 g bromine, after dripping 10-15 °C reaction under 1 hour, heating to 30-35 °C reaction 4 hours, HPLC detection raw material after the reaction is complete, cooling to 0 °C, by adding 66 g dithio ammonium dithiocarbamate, after adding 0 °C reaction 1 hour, then heating to 20-25 °C reaction 4 hours, filtering, to obtain 2-mercapto-4-pyridyl thiazole crude 81.7 g, crude product reflux in water for 2 hours, filtered to get after cooling to 2-mercapto-4-pyridylthiazole 80.2 g, yield 82.6percent as a pale yellow solid, HPLC purity was 99.7percent.2 g of the compound (V) was added in that order, Glacial acetic acid 10g, Stirring reflux reaction 5h (HPLC detection, raw materials ' 1percent).Filtration and drying yielded 1.62 g of the desired product (I) as an off-white solid. The yield of this step was 85.2percent (calculated as compound (V)), and the purity of liquid phase was 97percent -98percent.1.0g [4-(4-Pyridyi)-1 , 3-thiazol-2-yl]thio. were suspended in 5ml acetic anhydride and 0.69 tetramethylguanidsne were added at 0°C. The mixture was stirred for 2.5h, filtered and washed with 10ml diethylether and dried in vacuo. Yield: 0.73g 1H-NMR (CDCI3) 8 2.48 (s, 3H), 7.69 (m, 2H), 7.81 (s, 1 H), 8.59 (m, 2H) 3C-NMR (CDCI3) delta 30.5, 119.8, 120.5, 140.5, 150.5, 152.7, 155.9, 190.9

Molecular Weight:194.3
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:193.99724055
Monoisotopic Mass:193.99724055
Topological Polar Surface Area:82.3
Heavy Atom Count:12
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes