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CAS No. : | 126728-20-9 | MDL No. : | MFCD07644627 |
Formula : | C7H3Cl2N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QSNSZGYDLUPWSV-UHFFFAOYSA-N |
M.W : | 200.03 | Pubchem ID : | 22222228 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.35 |
TPSA : | 38.67 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.58 cm/s |
Log Po/w (iLOGP) : | 1.81 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 2.33 |
Log Po/w (MLOGP) : | 1.25 |
Log Po/w (SILICOS-IT) : | 2.73 |
Consensus Log Po/w : | 2.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.42 |
Solubility : | 0.0766 mg/ml ; 0.000383 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.2 |
Solubility : | 0.127 mg/ml ; 0.000637 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.19 |
Solubility : | 0.0128 mg/ml ; 0.0000641 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.9% | at 105℃; for 24 h; | To a 500 mL two-neck round bottom flask equipped with a thermometer and a reflux condenser, Intermediate 12 (10.0g, 0.061 mol) and phosphorous oxychloride (200 mL) were added, mixed uniformly, heated to reflux at 105 °C and stirred for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of phosphorus oxychloride. The remaining syrupy substance was poured onto 200 g of crushed ice, and immediately extracted 3 times with chloroform, 150 mL each time. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate), to give 10.36 g of a white solid product, yield 84.9percent. [0085] 1H-NMR (400 MHz, CDCl3) δ ppm: 9.34 (1H, m), 8.66 (1H, m), 7.76 (1H, m); EI-MS (m/z): 199.0[M]+ |
84.9% | at 105℃; for 24 h; | To a 500 mL two-neck round bottom flask equipped with a thermometer and a reflux condenser, Intermediate 12 (10.0 g, 0.061 mol) and phosphorous oxychloride (200 mL) were added, mixed uniformly, heated to reflux at 105° C. and stirred for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of phosphorus oxychloride. The remaining syrupy substance was poured onto 200 g of crushed ice, and immediately extracted 3 times with chloroform, 150 mL each time. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate), to give 10.36 g of a white solid product, yield 84.9percent.1H-NMR (400 MHz, CDCl3) δ ppm: 9.34 (1H, m), 8.66 (1H, m), 7.76 (1H, m); EI-MS (m/z): 199.0[M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | at 135℃; | (2) 1 g of intermediate B was added4With POCl3, PCl5The reaction was refluxed at 135 ° C to give the intermediate C4, Yield 54percent; reaction equation is as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A suspension of 2,4-dichloroquinazoline or <strong>[126728-20-9]2,4-dichloropyrido[2,3-d]pyrimidine</strong> (5 mmol) in 25% ammonia (30 mL) was heated under reflux for 1.5 h. The resulting precipitate was filtered off and washed with water (4 × 15 mL). The corresponding intermediate 4-amino-2-chloroquinazoline or pyrido[2,3-d]pyrimidine was used without purification and was treated with selenourea in ethanol (20 mL) in a stoichiometric ratio of 1:1.2, respectively. The mixture was heated during 4 h and then cooled. The resulting precipitate was filtered off and recrystallized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at -10℃; | To a 250 mL two-neck round bottom flask equipped with a thermometer and a constant pressure funnel, Intermediate 13 (10.36 g, 0.052 mol), N,N-diisopropylethylamine (7.35 g, 0.057 mol) and 1,2-dichloroethane (80 mL) were added; to the constant pressure funnel, a solution of 2,4-dichlorobenzylamine (10.03 g, 0.057 mol) in 1,2-dichloroethane (10 mL) was charged, and slowly added dropwise at -10 C. After completion of the dropwise addition, the system was stirred overnight. Precipitated solid was filtered, and the filter cake was purified through a silica gel column (eluent: petroleum ether/ethyl acetate), to give 16.35 g of a white solid product, yield 92.6%. [0087] 1H-NMR (400 MHz, DMSO) delta ppm: 9.57 (1H, m), 9.03 (1H, m), 8.79 (1H, m), 7.69 (1H, m), 7.64 (1H, m), 7.45 (2H, m), 4.79 (2H, d, J = 5.2 Hz); EI-MS (m/z): 339.2 [M+H]+. |
92.6% | With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at -10℃; | To a 250 mL two-neck round bottom flask equipped with a thermometer and a constant pressure funnel, Intermediate 13 (10.36 g, 0.052 mol), N,N-diisopropylethylamine (7.35 g, 0.057 mol) and 1,2-dichloroethane (80 mL) were added; to the constant pressure funnel, a solution of 2,4-dichlorobenzylamine (10.03 g, 0.057 mol) in 1,2-dichloroethane (10 mL) was charged, and slowly added dropwise at -10 C. After completion of the dropwise addition, the system was stirred overnight. Precipitated solid was filtered, and the filter cake was purified through a silica gel column (eluent: petroleum ether/ethyl acetate), to give 16.35 g of a white solid product, yield 92.6%.1H-NMR (400 MHz, DMSO) delta ppm: 9.57 (1H, m), 9.03 (1H, m), 8.79 (1H, m), 7.69 (1H, m), 7.64 (1H, m), 7.45 (2H, m), 4.79 (2H, d, J=5.2 Hz); EI-MS (m/z): 339.2 [M+H]+. |
With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; | EXAMPLE 1 Preparation of (R)-{4-[4-(2,4-Dichloro-benzylamino)-pyrido[2,3-d]pyrimidin-2-yl]-piperazin-1-yl}-piperidin-2-yl-methanone 2,4-Dichlorobenzylamine (211 mg, 1.2 mmol) was added to the stirred solution of <strong>[126728-20-9]2,4 dichloro-pyrido[2,3-d]pyrimidine</strong>(200 mg, 1 mmol) and N,N-diisopropylethylamine (266 muL, 1.5 mmol) in 1,2-dichloroethane (5 mL). The reaction mixture was stirred at room temperature for 12 h and then diluted with water (10 mL). The aqueous layer was extracted with CH2Cl2 and the combined organic layer was washed with water (2*10 mL), dried (Na2SO4) and concentrated in vaccuo to give (2-Chloro-pyrido[2,3-d]pyrimidin-4-yl)-(2,4-dichloro-benzyl)-amine as a yellow oil (185 mg) and was used as such in the next reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | EXAMPLE 357; 5-Bromo-3-(2-chloro-pyrido[2,3-d]pyrimidin-4-yl)-1,3-dihydro-indol-2-one; To a stirring mixture of NaH (260 mg, 6.50 mmol) in THF (20 mL) at 0 C. was added 5-bromooxindole (551 g, 2.60 mmol) in portion. Additional THF (5 mL×2) was used to make sure all the oxindole was added into the reaction flask. After stirred for 1 h, a solution of crude compound 356 in THF (5 mL×3) was added. The reaction was continued stir for 1 h at 0 C. and 24 h at room temp. A saturated NH4Cl solution (30 mL) was added into the reaction and the resulted red precipitate was collected by filtration. It was dried to give 361 mg (37%) the title Example 357. 1H NMR (400 MHz, DMSO-d6) delta 10.41 (s, 1H), 10.11 (s, 1H), 8.61 (m, 1H), 8.50 (s, 1H), 7.47 (m, 1H), 7.18 (m, 1H), 6.73 (m, 1H); MS (m/e) 376 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With N-ethyl-N,N-diisopropylamine; In ethanol; for 0.25h; | To a solutionof 3-amino-5-cyclopropyl-lH-pyrazole (800 mg, 6.5 mmol) and diisopropyl ethyl amine (2.51 g, 3.4 ml, 19.5 mmol) inEtOH (20 ml) was added 2,4- dichloropyrido [2,3-d] pyrimidine (Method82, 1.3 g, 6.5mmol). The mixture was stirred for15 minutes and the separated solid was filtered, washed with EtOH (5 ml). The solid was taken in a mixture of CHC13 (10 ml) and THF (5 ml) and refluxed for 15 minutes. The residue was filtered and dried to give the desired product(800 mg, 46%). 1H NMR5 0.73(m, 2 H),0. 98 (m, 2 H), 1.96(m,1 H), 6.51 (s,1 H), 7.61(m,1 H), 9.02(m,1 H), 9.03(m,1H). MS:m/z 289 (M+3), 287(M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine; In ethanol; at 20℃; | To a stirred solution of 2,4 dichloro-pyrido [2,3-d] pyrimidine (1.3 g, 6.7 mmol) and 3, 5-dimethoxybenzylamine (1.1 g, 6.7 mmol) in 30 mL EtOH at RT was added TEA (4 mL, 28.7 mmol). A precipitate formed that was filtered off and washed with cold EtOH followed by hexanes to give 1.8 g of the title compound (82%) as a solid. mp 185C (dec).'H-NMR (DMSO-d6) 8 : 9.5 (t, 1H), 8. 9 (dd, 1H), 8.7 (dd, 1H), 7.5 (m, 1H), 6.5 (d, 2H), 6.4 (t, 1H), 4.6 (d, 2H), 3.7 (s, 6H). MS (m/z, %): 331 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In tetrahydrofuran; at 20℃; for 6h; | 3-(2-Chloroquinazolin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (2) (1.0 g), 4- aminophenylboronic acid, pinacol ester (660 mg), toluene (7.5 mL), EtOH (7.5 mL), 2M aqueous Na2COs and tetrakis(thphenylphosphine) palladium (230 mg) were heated by microwave irradiation (1 hour, 120 C). After cooling, the reaction mixture was partitioned between ethyl acetate and water. The organic extracts were washed with brine and dried over MgSO4 and concentrated in vacuo to result in a dark syrup. Purification by RP HPLC gave the title compound as a yellow foam (0.52 g). A mixture of 2,4-dichloro-pyhdo[2,3-d]pyrimidine (200 mg, 1.00 mmol), morpholine (104mg, 1.20mmol) and triethyl amine (120 mg, 1.20 mmol) in 4 mL of THF was stirred at room temperature for 6 hours. Then the reaction mixture was diluted with 200 mL of ethyl acetate and the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The organic layer then was collected and dried over anhydrous sodium sulfate and concentrated to give 2-chloro-4-morpholin-4-yl-pyrido [2, 3-d] pyrimidine (4, 250mg, 100% yield) as a light yellow solid. HPLC: RT = 0.27 min; MS 251 , 253 [M+H]. |
In tetrahydrofuran; at 20℃; for 1h; | Crude <strong>[126728-20-9]2,4-Dichloro-pyrido[2,3-d]pyrimidine</strong> (6.66 g, 33.47 mol) was diluted in anhydrous THF (50 ml) under an inert atmosphere. To this was slowly added the appropriate amine (0.8 equiv) and the resultant mixture stirred at room temperature for 1 hour. The reaction was concentrated in vacuo and saturated sodium bicarbonate solution carefully added. The solid was then filtered and washed with more saturated sodium bicharbonate solution (100 ml) to give the desired compound in suitably clean form to be used without any further purification. 73a: NRR'=morpholino: m/z (LC-MSW, ESP): 251 [M+H]+, R/T=2.75 mins | |
1.1 g | With triethylamine; In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere; Cooling with ice; | 2,4-Dichloropyrido[2,3-d]pyrimidine (9) (1eq, 1g, 5 mmol) was dissolved in dry THF (100 mL) under inert gas and was kept in ice bath. A mixture of morpholine (1.05 eq, 456.75 muL, 5.25 mmol) and triethylamine (1.05 eq, 730.37 muL, 5.25 mmol) in 25 mL of dry THF was added dropwise to the previous solution with continuous stirring. The mixture was stirred at room temperature for 3 h. Then the the solvent was removed under reduced pressure. The residue was dissolved in chloroform (20 mL), extracted three times with saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to afford the title compound without further purification as white solid (1.1g, 90%). 1H-NMR (CDCl3): delta 3.80 (m, 4H), 3.88 (m, 4H), 7.28 ( dd, J = 4.2 Hz, J = 8.3 Hz, 1H), 8.12 ( dd, J = 1.8 Hz, J = 8.3 Hz, 1H), 8.95 (dd, J = 1.8 Hz, J = 4.2 Hz, 1H). LCMS, tR = 2.34 min, m/z C11H11ClN4O [M+ H]+ = 251.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; sodium iodide; at 100℃; for 1h;Microwave irradiation; | Example 1; Cyclopropanesulfonic acid {5-methyl-3-r4-(5-methyl-1 H-pyrazol-3-ylamino)-pvrido[2,3- dlpyrimidin-2-v?-3-aza-bicvclor3.1.Olhex-1 -ylVamide; (A) Preparation of 2-Chloro-N-(3-methyl-1 H-pyrazol-5-yl) pyridor2.3-dlpyrimidine-4- arnine; Heat a mixture of <strong>[126728-20-9]2,4-dichloropyrido[2,3-d]pyrimidine</strong> (5.Og, 1.0eq.), 3-methyl-1 H- pyrazol-5-amine (2.42g, 1.0eq.), Diisopropyl ethyl amine (3.54g, 4.76 mL, 1.1 eq.) and sodium iodide (4.09g, 1.1eq.) to 100C in Microwave reactor for 1 hour. Concentrate under high vacuum, dilute with EtOAc, filter the solid and wash with water. Dry under high vacuum overnight to obtain 9.75g the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The appropriate 2,4-dichloro-pyridopyrimidine (3)(1 equivalent) was suspended in CH2Cl2 (4 ml of solvent per mmol of material) and to this mixture was added triethylamine (1 equivalent). The resultant orange solution was then cooled to 0 C. and the appropriate amine (R2H) (1 equivalent) added dropwise as a 0.1 M solution in CH2Cl2 over 5 minutes. The mixture was stirred for a further 45 minutes before it was diluted with water and extracted with CH2Cl2 (×2). The organic extracts were dried using MgSO4, filtered and concentrated in vacuo to give a crude solid that was purified by flash chromatography (SiO2) using Hexanes:EtOAc (2:3) as eluent to give the desired product (1 equivalent) which was diluted in dimethylacetamide (0.7 M) and the appropriate amine (R1H) (2.5 equivalents) added. The reaction mixture was heated to 60 C. for 16 hours. Upon completion the reaction mixture was submitted for preparative HPLC purification to give the desired pyridopyrimidine-2,4-diamines, as detailed below: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; In tetrahydrofuran; water; Petroleum ether; | (a) 2,4-Dichloropyrido[2,3-d]pyrimidine (5.6 g, 0.028 mol), N-methylaniline (2.29 g, 0.028 mol) and sodium acetate (2.56 g, 0.032 mol) were stirred at room temperature in a mixture of tetrahydrofuran (300 ml) and water (150 ml) for 4 days. The solvent was evaporated under vacuum and the aqueous residue extracted (x2) with chloroform. The combined chloroform extracts were washed with water, dried and evaporated to dryness to give a brown solid. This was treated with petroleum ether, filtered and dried to give 2-chloro-4-(N-methylphenylamino)pyrido-[2,3-d]pyrimidine (5.6 g) which was identified by n.m.r. and mass spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred solution of 2, 4-dichloro-pyrido [2,3-d] pyrimidine (0.75 mmol) and DIPEA (1.5 mmol) in 3 mL DMSO was added 0.75 mmol of an amine corresponding to formula (V), Scheme 1, STEP 1, at RT. The mixture was stirred at RT for one hr, then 2.25 mmol of an amine corresponding to formula (VIl), Scheme 1, STEP 2, and additional DIPEA (2.25 mmol) were added, and the mixture heated at 90C for two hr. Example 32 N4-(3,4-Dimethoxy-benzyl)-N2-(3-phenyl-propyl)-pyrido[2,3-d]pyrimidine-2, 4-diamine The compound was isolated and purified from the crude reaction mixture by direct injection onto a reversed-phase preparative HPLC using a step gradient of acetonitrile/water containing 0. 1% ammonium hydroxide as an lutant. Fractions containing the compound were combined and concentrated to give a solid. m. p. 190- 2C.'H-NMR (d6-DMSO) : 8 8.6 (dd, 1H), 8.4 (dd, 1H), 7.2 (m, br, 3H), 7.1 (m, br, 2H), 7.0 (m, br, 2H), 6.8 (m, br, 2H), 4.6 (m, br, 2H), 3.7 (d, br, 6H), 3.3 (m, br, 2H), 2.6 (m, br, 2H), 1.8 (m, 2H). MS (m/e, %): 431 (M++1, 50), 430 (M+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethanol; at 70℃; | Intermediate 23; 2-Chloro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyridor2,3-dlpyrimidin-4-amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 167 mg, 1.72 mmol), 2,4- dichloropyrido[2,3-d]pyrimidine (500 mg, 2.50 mmol) were suspended in ethanol (10 mL) and TEA (0.24mL, 1.72 mmol) was added. The reaction mixture was heated at 700C overnight and the title product was obtained after filtration (421mg).1H NMR (300 MHz, DMSO-d6) delta ppm 11.33 (s, 1 H) 9.16 (d, 1 H) 9.01 (s, 1 H) 7.54-7.72(m, 3H) 3.75 (s, 3 H). 103496-1PLCMS: 261 [M+H]4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 60℃; for 0.333333h;Microwave irradiation; | EXAMPLE 20 Synthesis of 4-carboxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)- pyrido[2,3-d]pyrimidine (Compound 123-49)20.1 Preparation of 2-chloro-4-(2-furanyl)-pyrido[2,3-d]pyrimidineA mixture of 2,4-dichloro-pyrido[2,3-d]pyrimidine (200 mg, 1.0 mmol), 2-(tributylstannyl)- furan (0.35 ml, 1.1 mmol), bis-(triphenylphosphine)palladium dichloride (35 mg, 0.05 mmol) and degassed dimethylformamide (10 ml) was heated in a microwave reactor at 60 C for 20 minutes, then allowed to cool and ethyl acetate added. The mixture was washed with water and brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by automated flash chromatography (Presearch Combiflash Rf) on silica, with methanol in dichloromethane (0% to 10% gradient) as eluent, to provide 2-chloro-4-(2-furanyl)-pyrido[2,3-d]pyrimidine as a yellow solid (217 mg, 94%).Characterising data for the compound are as follows: 1H NMR (400 MHz, CDCI3) delta 9.40 (1 H, dd), 9.30 (1 H, m), 7.80 (1 H, m), 7.70 (1 H, 7.60 (1 H, dd), 6.70 (1 H, m) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tri-n-butyl-tin hydride;tetrakis(triphenylphosphine) palladium(0); In toluene; for 3h;Inert atmosphere; Heating; | To a degassed, stirred solution of 2,4-dichloro-pyrido[2,3-d]pyrimidine (150 mg, 0.75 mmol) and tributyltin hydride (0.22 ml, 0.83 mmol) in toluene (10 ml) was addedtetrakis(triphenylphosphine)palladium(0) (87 mg, 75 muiotatauiotaomicronIota). The solution, kept under argon, was immersed in a preheated oil bath (100C) and stirred at that temperature for 3 hours. The mixture was cooled down to ambient temperature, concentrated in vacuo to about 2 ml and diluted with acetonitrile. It was extracted 3 times with hexane. The acetonitrile layer was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (eluent gradient: 0% to 6% methanol in dichloromethane). The title compound was obtained as a white solid. 1H NMR (CDCI3): 7.69 (dd, 1 H), 8.40 (dd, 1 H), 9.33 (dd, 1 H), 9.42 (s, 1 H). | |
With tri-n-butyl-tin hydride;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃; for 3h;Inert atmosphere; | h) Preparation of 2-chloro-pyrido[2,3-d]pyrimidine: To a degassed, stirred solution of 2,4-dichloro-pyrido[2,3-d]pyrimidine (150 mg, 0.75 mmol) and tributyltin hydride (0.22 ml, 0.83 mmol) in toluene (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 mmol). The solution, kept under argon, was immersed in a preheated oil bath (100 C.) and stirred at that temperature for 3 hours. The mixture was cooled down to ambient temperature, concentrated in vacuo to about 2 ml and diluted with acetonitrile. It was extracted 3 times with hexane. The acetonitrile layer was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (eluent gradient: 0% to 6% methanol in dichloromethane). The title compound was obtained as a white solid. 1H NMR (CDCl3): 7.69 (dd, 1H), 8.40 (dd, 1H), 9.33 (dd, 1H), 9.42 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With triethylamine; In ethanol; at 70℃; for 5h; | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1. |
Tags: 126728-20-9 synthesis path| 126728-20-9 SDS| 126728-20-9 COA| 126728-20-9 purity| 126728-20-9 application| 126728-20-9 NMR| 126728-20-9 COA| 126728-20-9 structure
[ 938443-20-0 ]
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
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P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
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P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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