* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Polish Journal of Chemistry, 1992, vol. 66, # 5, p. 787 - 790
2
[ 19829-29-9 ]
[ 5402-20-0 ]
[ 2645-22-9 ]
Reference：
[1] Journal of the Chemical Society, 1958, p. 1853
[2] Anales de la Real Sociedad Espanola de Fisica y Quimica, 1958, vol. <B> 54, p. 383,386
3
[ 2645-22-9 ]
[ 7732-18-5 ]
[ 7722-84-1 ]
[ 64-19-7 ]
[ 5402-20-0 ]
Reference：
[1] Journal of the Chemical Society, 1958, p. 1853
1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(pyridin-4-ylsulfanyl)-1H-pyrimidine-2,4-dione; compound with trifluoro-acetic acid[ No CAS ]
1-[3,4-Bis-(4-methoxy-benzyloxy)-benzyl]-4-[(4S,5R,6S)-2-(4-methoxy-benzyloxycarbonyl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-en-3-ylmethylsulfanyl]-pyridinium; bromide[ No CAS ]
With ammonia; In methanol; DMF (N,N-dimethyl-formamide); for 5h;
<strong>[2645-22-9]4,4'-dithiodipyridine</strong> (79 mg, 0.36 mmol) and methanolic ammonia (20 eq.) were added to DMF (0.5 ml) containing Boc-Am7(Ac)-NHMe (60 mg, 0.18 mmol), and stirred for 5 hours. After the reaction solution was concentrated, the resulting oily product was purified by flash silica gel chromatography (1.5*30 cm, chloroform) and freeze-dried to obtain the title compound (43 mg, 0.11 mmol, 61percent yield). HPLC retention time: 5.6 min; HRMS (FAB, dithiodiethanol), 400.1766 [M+H], C18H29O3N3S2 (400.1729).
cyclo(-L-Am7(S4Py)-D-Tyr(Me)-L-Ile-D-Pro-)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
13%
With methanol; ammonia; In DMF (N,N-dimethyl-formamide); for 8h;
DMF (1 ml) containing cyclo(-L-Am7(Ac)-D-Tyr(Me)-L-Ile-D-Pro-) (100 mg, 0.17 mmol) was mixed with 4,4'-dithiopyridine (75 mg, 0.34 mmol) and methanolic ammonia (20 eq.) and stirred for 8 hours. After the reaction solution was concentrated, the powder product was purified by flash silica gel chromatography (4.x.30 cm, 1percent methanol/chloroform) to obtain the title compound. The yield was 13 mg (13percent). HPLC retention time: 6.5 min; HRMS (FAB, dithiodiethanol), 656.2934 [M+H], C33H45O5N5S2 (656.2940).
a 7-(Pyridin-4-yl)thioimidazo[5,1-b]thiazole A solution of 2.5 g of 7-iodoimidazo[5,1-b]thiazole in 40 ml of dry THF was cooled in ice. A 0.95 M ethylmagnesium bromide/THF solution (11.7 ml) was added to the cooled solution under an argon atmosphere. The mixture was stirred at that temperature for 40 min. 4,4'-Dipyridyl disulfide (3.3 g) was added thereto, and the mixture was stirred at room temperature for 18 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was then extracted with ethyl acetate twice. The extract was washed with brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane:methanol =30:1 to 20:1) and by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to prepare 1.09 g of 7-(pyridin-4-yl)thioimidazo[5,1-b]thiazole. NMR (CDCl3) delta: 6.95-7.0 (3H, m), 7.53 (1H, d, J=3.9Hz), 8.16 (1H, s), 8.3-8.4 (2H, m)
This shows the preparation of N-(tert-butyl)-5-(pyridin-4-ylthio)thiophene-2-sulfonamide.To a solution of 72-BuLi in hexanes (2.5 M, 2.4 rnL) in THF (20 mL) at -78 0C was added 5-bromo-iV-(terf-butyl)thiophene-2-sulfonamide (895 mg) in THF (3 mL) dropwise. The reaction mixture was stirred at this temperature for 30 min then <strong>[2645-22-9]4,4'-dithiodipyridine</strong> (661 mg) in THF (3 mL) was added which caused the formation of a precipitate. The mixture was allowed to warm to RT and stirred for 20 h. The reaction mixture was then partitioned between ethyl acetate and water, and the organic phase washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue purified by silica gel column chromatography, eluting impurities with 2 : 1 zso-hexane / ethyl acetate, and then with 1 : 1 /so-hexane / ethyl acetate to give the title compound N-(tert- butyl)-5-(pyridin-4-ylthio)thiophene-2-sulfonamide (297 mg).1H NMR (400 MHz, DMSO) delta 8.43 (s, 2H), 7.61 (d, IH), 7.27 - 7.26 (m, IH), 7.00 (d, 2H)5 4.62 (s, IH), 1.34 (s, 9H).
3-(pyridin-4-ylsulfonyl)-5-chloroindole-2-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 63 Preparation of 3-(pyridin-4-ylsulfonyl)-5-chloroindole-2-carboxamide Using the procedure described in Example 30 and 31, except substituting bis(pyridin-4-yl)disulfide for di(2-thiazolyl)disulfide, the title compound was obtained, mp>260° C. dec. FAB maes spectrum: m/e=336 (M+1)
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