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Structure of 2345-51-9 * Storage: {[proInfo.prStorage]}
* 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] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5017 - 5020
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 1, p. 193 - 197
2
[ 186581-53-3 ]
[ 2345-51-9 ]
[ 32804-66-3 ]
Reference：
[1] Acta Chemica Scandinavica (1947-1973), 1952, vol. 6, p. 893,898
[2] Annales de Chimie (Cachan, France), 1956, vol. <13>1, p. 161,184,186
[3] Synthetic Communications, 1995, vol. 25, # 13, p. 2019 - 2027
3
[ 124-38-9 ]
[ 106-96-7 ]
[ 2345-51-9 ]
Yield
Reaction Conditions
Operation in experiment
98.3%
With magnesium In tetrahydrofuran at 20 - 60℃; for 3 h; Inert atmosphere
After adding dropwise, 120 g of bromopropyne was added dropwise under the protection of nitrogen in a 1000-ml three-necked flask with 24 g of magnesium turnings and 300 ml of tetrahydrofuran as a solvent, and the reaction was carried out at room temperature for 60 minutes. The excess carbon dioxide was heated to 60 And the reaction mixture was poured into a saturated aqueous ammonium chloride solution cooled to 200 mg, extracted, separated and separated. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The organic layer was dried over anhydrous sodium sulfate The crude product of 3-butynoic acid was recrystallized from 50 ml of methyl t-butyl ether and filtered to obtain crystals. The crystals were dried to give 70 g of 3-butynoic acid as a pure product, Was 98.3percent.
Reference：
[1] Patent: CN105481683, 2016, A, . Location in patent: Paragraph 0021; 0022
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9266 - 9270[3] Angew. Chem., 2013, vol. 125, # 35, p. 9436 - 9440
[4] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5561 - 5583
[5] Journal of the American Chemical Society, 2015, vol. 137, # 10, p. 3482 - 3485
[6] Synthetic Communications, 1995, vol. 25, # 13, p. 2019 - 2027
4
[ 927-74-2 ]
[ 2345-51-9 ]
Yield
Reaction Conditions
Operation in experiment
76%
With sodium periodate; sodium dichromate; nitric acid In waterCooling with ice
Preparation 1: Synthesis of 3-butynoic acidOH03-butynoic acid was prepared from the oxidation of 3-butyn-1-oI and following the reported procedure (Schmieder-van de Vondervoort, L. et a., P. L. SynIett2002, 2002, 0243). Water (45 mL) was added to a 150 mL single neck RBF fitted with a magnetic. stirrer bar. 65percent HNO3 (0.17 mL, 5 molpercent, 2.5 mmol), Na2Cr2O7 (0.15 g, I molpercent, 0.5 mmol) and NaIO4 (23.53 g, 2.2 eq., 110 mmol) were subsequently added to the RBF and the mixture was stirredvigorously on an ice bath for 15 mm. 3.78 mL of 3-butyn-1-ol (1 eq., 50 mmol) dissolved in45 mL of chilled water was added to this mixture slowly and the reaction mixture was left for18 — 24 hrs (ice bath was not removed to let the ice melt and temperature of reaction mixturerise slowly to rt). After this time, the product was extracted in diethyl ether (80 mL X 6). All ofthe fractions were combined and dried over anhydrous magnesium sulphate. The solventwas removed usinga rotary evaporator to give an orange/yellowish viscous liquid.Subsequent addition of dichloromethane and removal of solvent on a rotary evaporator (under vacuum) 4-5 times gave 3.20 g of an off white/yellowish solid (38 mmol, yield 76percent).1H NMR (400 MHz, CDCI3) 6 3.38 (d, 2H, J 2.7 Hz), 2,25 (t, IH, J = 2.7 Hz); 13C NMR(400 MHz, CDCI3) 6 173.8, 74.8, 72.4, 25.6
Reference：
[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 29, p. 7491 - 7494[2] Angew. Chem., 2014, vol. 126, # 29, p. 7621 - 7624,4
[3] Patent: WO2015/160307, 2015, A1, . Location in patent: Page/Page column 23; 24
[4] Synlett, 2002, # 2, p. 243 - 246
[5] Angewandte Chemie - International Edition, 2018, [6] Angew. Chem., 2018, vol. 130, # 45, p. 15033 - 15037,5
[7] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5017 - 5020
[8] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15131 - 15143
[9] Organic Letters, 2014, vol. 16, # 20, p. 5394 - 5397
[10] Tetrahedron Letters, 1997, vol. 38, # 29, p. 5073 - 5076
[11] Journal of Organic Chemistry, 1999, vol. 64, # 14, p. 5053 - 5061
[12] European Journal of Organic Chemistry, 2013, # 14, p. 2906 - 2913
[13] Journal of the Chemical Society, 1949, p. 606
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 1981 - 1987
[15] Journal of the Chemical Society [Section] C: Organic, 1966, p. 135 - 139
[16] Journal of Medicinal Chemistry, 1987, vol. 30, # 1, p. 193 - 197
[17] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2642 - 2657
[18] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5843 - 5845
[19] Journal of the American Chemical Society, 2010, vol. 132, # 11, p. 3640 - 3641
[20] Patent: WO2015/100277, 2015, A9, . Location in patent: Paragraph 00209
[21] Synlett, 2017, vol. 28, # 8, p. 944 - 950
5
[ 10024-18-7 ]
[ 124-38-9 ]
[ 5732-10-5 ]
[ 2345-51-9 ]
Reference：
[1] Synthesis, 1981, # 11, p. 875 - 878
6
[ 463-49-0 ]
[ 124-38-9 ]
[ 5732-10-5 ]
[ 2345-51-9 ]
Reference：
[1] Synthesis, 1981, # 11, p. 875 - 878
7
[ 2936-44-9 ]
[ 124-38-9 ]
[ 5732-10-5 ]
[ 2345-51-9 ]
Reference：
[1] Synthesis, 1981, # 11, p. 875 - 878
N-[4-((3-bromophenyl)amino)quinazolin-6-yl]buta-2,3-dienamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
56%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0℃; for 1.5h;
To a solution of <strong>[169205-78-1]6-amino-4-[(3-bromophenyl)amino]quinazoline</strong> (316 mg, 1.0 mmol), and 3-butynoic acid (173 mg, 2.06 mmol) in DMF (5 mL) stirred under nitrogen at 0 C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (384 mg, 2.0 mmol). After 1.5 hours the reaction was quenched with 0.1 M HCl solution (10 mL). The yellow precipitate was collected by Buchner filtration and washed with water followed by acetone. The solid was taken up into acetone with the addition of triethylamine. The formed solution was filtered through a 2-inch silica gel eluding with 50% acetone/CH2Cl2. The filtrate was collected and concentrated under reduced pressure to give the title compound as a yellow solid (247 mg, 56%), mp 268-270 C. 1H NMR [(CD3)2SO]: delta 10.39 (s, 1H, NH), 9.93 (s, 1H, NH), 8.76 (d, J=2.2 Hz, 1H, H5), 8.58 (s, 1H, H2), 8.18 (s, 1H, H2'), 7.87 (dt, J=9.0, 1.9 Hz, 2H, H7, H8), 7.79 (d, J=8.8 Hz, 1H, H6'), 7.34 (t, J=7.9 Hz, 1H, H5'), 7.29 (d, J=8.3 Hz, 1H, H4'), 6.07 (t, J=6.5 Hz, 1H, CH=C=CH2), 5.49 (d, J=6.6 Hz, 2H, =C=CH2). Mass Spectrum (APCI): 382.8 (88, 81BrMH+), 381.8 (19, 81BrM+), 380.7 (100, 79BrMH+). Calculated for C18H13N4BrO.0.8H2O.0.8C3H6O: C, 55.42; H. 4.42; N, 12.68%. Found: C, 55.13; H, 4.17; N, 12.87%.
N-(2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)buta-2,3-dienamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
3-Butynoic acid was stirred with 1.5 equivalents of Mukaiyama reagent (2-chloro-1-methyl pyridinium iodide) in dry dichloromethane at room temperature for one hour without any base. After one hour, a solution of the desired amine (1.1 eq.) and triethylamine (1.5 eq.) in dry dichloromethane was added to the 3-butynoic acidmixture drop-wise. A slight exotherm was observed during this step, after which the reaction mixture was stirred for another half anhour. After this time, the dichioromethane was removed usinga rotary evaporator and ethyl acetate was added to the solid residue which was then transferred to a separatory funnel. The organic layer was washed 2 times with water and dried on anhydrous sodium sulphate. Solvent was evaporated to provide the crude product which was purified by column chromatography. Yields were found to be sensitive to the amount of triethylamine used withexcess TEA giving poorer yields. Synthesis of N-(2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)buta-2,3-dienamide (1 e) H?N11 ?%03-Butynoic acid (preparation 1, 0.27 g, I eq., 3.2 mmol) and 1.22 g of 2-chloro-1-methyl pyridinium iodide (1.5 eq., 4.8 mmol) were charged in a 25 mL two neck oven dried RBF fitted with a magnetic stirrer bar. 10 mL dry dichloromethane was added to it and the mixture was stirred under nitrogen for 1 hr. 0.66 g of respective amine (7-amino-4-(trifluoromethyl)-2H-chromen-2-one) was added (0.9 eq. 2.9 mmol) in portions (solid) followed by addition of0.60 mL of triethylamine (1.5 eq. respective to amine, 4.3 mmol) in 5 mL dry dichioromethane after which the reaction mixture was stirred for another half an hour. After due time dichloromethane was evaporated and product was purified by flash column chromatography (30 - 40% EA in hexane) to get a yellow solid.1H NMR (400 MHz, CDCI3) 67.84 (s, IH), 7.81 (d, IH, J = 2.1 Hz), 7.66 (dd, IH, J = 1.7, 8.9Hz), 7.49 (dd, I H, J = 2.1, 8.8 Hz), 6.70 (s, I H), 5.82 (t, 1 H, J = 6.6 Hz), 5.46 (d, 2H, J = 6.6Hz); 13C NMR (400 MHz, CDCI3) 6 212.2, 162.6, 159.1, 155.3, 142.1, 126.1, 126.0, 115.9,113.9, 113.8, 109.5, 107.2, 91.7, 82.1; ESI-MS calculated for C14H8F3N03 [M+H] m/z296.05,found 296.16F
2-[8-methyl-2-(3-methyl-1-benzofuran-2-yl)-5-(1-phenylethoxy)quinolin-4-yl]acetic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1%
With copper(l) chloride; In tetrahydrofuran; at 80℃; for 12h;
A. 2-[8-Methyl-2-(3-methyl-1-benzofuran-2-yl)-5-( 1-phenylethoxy)quinolin-4-yllacetic acid. To a 100-mL round-bottom flask was placed a solution of 2-methyl-5-(1-phenylethoxy)aniline (1 g,4.40 mmol,Intermediate 52) in THF (30 mL) then 3-methyl-i-benzofuran-2-carbaldehyde (700 mg,4.37 mmol),CuC1 (430 mg,4.39 mmol),and but-3-ynoic acid (300 mg,3.57 mmol) were added. The reaction was stirred at 80C for 12 h,quenched by the addition of water,and extracted with EtOAc. The organic extracts were combined,washed with brine,dried over anhydrous Na2SO4,and concentrated under reduced pressure. The crudeproduct was purified by Prep-HPLC (Column,X Bridge Prep C18 Sum OBDTM19*100mm; mobile phase,water with 0.05% TFA and CH3CN (10.0% CH3CN up to 85.0% in10 mm,up to 95.0% in 1.5mm,down to 10.0% in 1.5mm); Detector,uv 254nm) affording 11 mg (1%) of the title compound as a yellow solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C29H26NO4: 452.2 (M+H); Found: 452.2. 1H NMR (400 MHz,DMSO-d6): oe 12.48 (brs,1H ),7.95 (s,1H ),7.78 (d,J 7.6 Hz,1H ),7.67 (d,J= 8.4 Hz,1H ),7.47-7.43 (m,3H),7.37-7.31 (m,4H),7.26-7.23 (m,1H ),6.64 (d,J= 8.4 Hz,1H ),5.61 (q,J= 6.0 Hz,1H ),4.56 (d,J= 16.8 Hz,1H ),4.39 (d,J= 16.8 Hz,1H ),2.84 (s,3H),2.61 (s,3H),1.69 (d,J 6.0 Hz,3H). HPLC purity (254 nm): 98.7%.
N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)buta-2,3-dienamide trifluoroacetate[ No CAS ]
With bis(acetylacetonate)oxovanadium; at 80℃; for 8h;
10 mmol (5-chloro-1H-indole 3-methyl)methylamine, 12 mmol 3-butynoic acid and 10 mL ionic liquid [HMIm]C1 were added to the reaction flask, stirred until dissolved, then 0.6 mmol was added The catalyst Vo(acac)2 was stirred for about 0.5 h, then the temperature was raised to 80 C, and the reaction was stirred for 8 h. The reaction progress was detected by thin layer chromatography. After the reaction was completed, the temperature was cooled to room temperature, 60 mL of saturated sodium carbonate solution was added, and the reaction was stirred. After adding 0.5 mL of ethyl acetate to the reaction system, the organic layer was combined and the organic layer was washed twice with brine brine, Recrystallization from 95% ethanol as a solvent gave the desired product in a yield: 86%.
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.05h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.0166667h;
Stage #3: 3-butynoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine; (S)-2-[(9H-fluoren-9-yl)methoxy]carbonyl}amino-3-(prop-2-enoxy)propanoic acid Further stages;
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