* 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.
cyclopent-1-ene-1,2-dicarboxylic acid 1-[(3-fluoro-3'-methoxy-biphenyl-4-yl)-amide] 2-hydroxyamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With O-(tert-butyl)hydroxylamine hydrochloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃; for 18.0h;
A solution of CYCLOPENT-L-ENE-1, 2-DICARBOXYLIC acide monoamide- (lequ, Immol) and TBTU (LEQ, LMMOL) in DIMETHYLFORMAMIDE (3ml) was stirred for 10 minutes at room temperature. Afterwards O-t-butylhydroxylamine hydrochloride (LEQ, LMMOL) and N, N- diisopropylethylamine (LEQ, LMMOL) was added and the solution was stirred for 18h at room temperatures. The solvent was removed in vacuum and the residue was purified by HPLC to give the pure product.
2-((3-fluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)carbamoyl)cyclopent-1-enecarboxylic acid calcium salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With calcium hydroxide; In methanol; dichloromethane; at 25.0℃;
300.4 mg of Vidofludimus free acid was dissolved in 18 mL of DCM/MeOH (3:1) and sonicated for 8 minutes. 31.5 mg of calcium hydroxide was suspended in 3 mL of DCM/MeOH (3:1); this was slowly added to the Vidofludimus free acid solution. The slight suspension was stirred overnight at 25C. The solvent was partially evaporated under nitrogen flow at 25C. A thick light yellow suspension was observed. The solid was recovered by filtration and washed with DCM/MeOH (3:1). The material was dried for 15 min under vacuum at 25C. The material was shown to be crystalline using the methods described in the following.From elemental analysis, the ratio of fluorine to calcium was calculated. The elemental composition is essentially consistent with a hemi-calcium-salt.The Raman spectrum of the newly formed compound demonstrated differences to that of the free acid (see Figure 3 for both spectra.). Note that a Raman spectrum that is not simply the superposition of the free acid, the salt former and the solvent spectra, e.g., a Raman spectrum where new peaks or shifted peaks are observed, may correspond to a salt.However, from the Raman spectrum alone, it cannot be determined whether crystalline salt formation has occurred. Peak shifts could also be due, in principle, to complexation of the free acid and salt former as an amorphous product, to polymorphs of either the free acid or salt former, to impurities, or to degradation products. Therefore, the integrity of the molecular structure was confirmed by lH-NMR.In addition, the powder X-ray diffraction shown in Figure 5 show that crystalline material was obtained, however with a pattern different from that of the free acid (see Figure 6). With light microscopy the crystals were visualized (Figure 4), DSC (differential scanning calorimetry) demonstrated a melting point of about 155C (indicating a melting of a solvate and of a non-solvated form), TG-FTIR (thermogravimetric analyzer-coupled Fourier-Transform Infrared) indicates that probably a methanol solvate and a hydrate were formed and dynamic vapor sorption revealed desolvation followed by 0.3% water uptake at about 85% r.h. and 0.4% water uptake at 95% r.h. (not reversible).
N-(3-fluoro-3'-methoxy[1,1'-biphenyl]-4-yl)cyclopent-1-ene-1,2-dicarboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
With thionyl chloride; ammonia; sodium sulfate; In dichloromethane; for 4.0h;Reflux;
I mL of concentrated ammonia and 3 g of anhydrous sodium sulfate were added into 5mL of dchioromethane, sLirred in ice bath for3 () miii. This reaction gave the solution ofammonia in methylene chloride. 5 mL of dichloromethane and I g of thionyl chloridewas added into 1 50 lug (0.42 mmol) of vidofiudimus, reflux reaction for 4 h. Theorganic solvent was removed by concentration under reduced pressure. 2 mL ofdichloromethane was added with stirring in ice bath, then 2.5 mL of the solution ofammonia in methylene chloride was added inLo the reaction dropwise. After thaL, the reaction was wamied up to room temperature, stirred continuously for 5 h. Then, 10 rnLof dichioromeihane and 5 mL of water were added, After stirring for 5 mm, the liquidwas separated. The organic phase was washed with 5 rnL of water twice, dried withanhydrous sodium sulfate, concentrated and purified by column chromatography. 108mg of FD1 was achieved, with yield of 73%.
N1-(3-fluoro-3'-methoxy[1,1'-biphenyl]-4-yl)-N2-methylcyclopent-1-ene-1,2-dicarboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
With thionyl chloride; sodium sulfate; methylamine; In dichloromethane; water; for 4.0h;Reflux;
40% methylamine aqueous solution and 3 g of anhydrous sodium sulfate were addedinto 5 mL of dichioromethane, stirred in ice bath for 30 mm. This reaction gave thesolution of methylamine in methylene chloride. 5 mL of dichioromethane and I g ofthionyl chloride were added into 150 mg (0.42 mmol) of vidofiudimus, reflux reactionfor 4 h. The organic solvent was removed by concentration under reduced pressure. 4mL of dichloromethane was added with stirring in ice bath, then I mL of the solution ofmethylamine in methylene chloride was added into the reaction dropwise. After that, thereaction was warmed up to room temperature, stirred continuously for 5 h. Then, 5 mLof dichloromethane and S mL of water were added. After stirring for 5 mill, the liquidwas separated. The organic phase was washed with 5 mL of water for three times, driedwith anhydrous sodium sulfate, concentrated and purified by column chromatography.121 mg of FD2 was achieved, with yield of 78%.
ethyl 2-((3-fluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)carbamoyl)cyclopent-1-ene-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79.5%
With thionyl chloride; for 3.0h;Reflux;
5 mL of ethanol was added into 380 mg of thionyl chloride, which gave the solution ofthionyl chloride in ethanol.5 mL of ethanol was added into 150 ing (0.42 mmoi) of vidofiudimus, and then 1 mL ofthe solution of thionyl chloride in ethanol was added into the reaction. After warming upfbr refiux reaction for3 h, the solvent was removed under reduced pressure. 5 niL ofethanol was added and the thionyl chloride was removed by concentration under reducedpressure twice. Then 10 mL of dichloromethane and 5 mL of water were added. Afterstirring for 10 mm, the liquid was separated. The organic phase was washed with 5 mLof water for three times, dried with anhydrous sodium sulfate, filtered, concentrated andpurifIed by column chromatography. 128 mg of FD3 was achieved, with yield of 79.5%.
With thionyl chloride; In ethanol; for 3.0h;Reflux;
5 mL of anhydrous methanol was added into 380 mg of thionyl chloride, which gave thesolution of dichlorosulfoxide in methanol. 5 mL of ethanol was added into 150 mg (0.42mmol) of <strong>[717824-30-1]vidofludimus</strong>, and then 1 rnL of the solution of dichlorosulfoxide in methanolwas added into the reaction. After warming up for refiux reaction for 3 h, the solvent wasremoved under reduced pressure. 5 niL of ethanol was added and the thionyl chloridewas removed by concentration under reduced pressure twice. Then 10 mL ofdichloromethane and 5 mL of water were added. After stirring for 10 mm, the liquid wasseparated. The organic phase was washed with 5 mL of water for three times, dried withanhydrous sodium sulfate, filtered, concentrated and purified by column chromatography.134 mg of FD5 was achieved, with yield of 86.5%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
