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CAS No. : | 23794-16-3 | MDL No. : | MFCD09702373 |
Formula : | C7H5BrClNO | Boiling Point : | 321.2°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 234.48 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.31 |
TPSA : | 29.96 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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.61 |
Log Po/w (XLOGP3) : | 2.29 |
Log Po/w (WLOGP) : | 2.31 |
Log Po/w (MLOGP) : | 1.2 |
Log Po/w (SILICOS-IT) : | 2.84 |
Consensus Log Po/w : | 2.05 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.01 |
Solubility : | 0.23 mg/ml ; 0.000982 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.56 |
Solubility : | 0.651 mg/ml ; 0.00278 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.85 |
Solubility : | 0.0328 mg/ml ; 0.00014 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 | UN#: | 3261 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 |
---|---|---|
60% | In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In ethanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol for 6h; Heating; | |
In ethanol at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Ethyl isobutyrate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In tetrahydrofuran at -78 - 20℃; | 141.a a) 2-[2-(2-Chloro-pyridin-4-yl)-2-oxo-ethyl]-4-methyl-3-oxo-pentanoic acid ethyl ester. 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (500 mg) is stirred in a mixture of 20 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Ethyl isobutyrate (337 mg) in 5 ml THF is added drop wise to a solution of LiHMDS (2.1 ml 1.0 M solution) in 5 ml THF at - 78 0C. After stirring for 2 hours at -78 0C 2-bromo-1-(2- chloro-pyridin-4-yl)-ethanone (see above) dissolved in 3 ml THF is added drop wise. The reaction mixture is allowed to warm to room temperature overnight. Aqueous NH4Cl solution is added and the mixture is extracted with ethyl acetate. After removal of the solvent the title compound is obtained as a pale yellow oil. 1H-NMR (400 MHz, DMSO-d6): 1.07 (d, 3H), 1.10 (d, 3H), 1.19 (t, 3H), 2.98 (sept, 1 H), 3.50- 3.68 (m, 2H), 4.13 (q, 2H), 4.33 (t, 1H), 7.84 (d, 1H), 7.96 (s, 1H), 8.63 (d, 1H). MS (ESI+) m/z: 312 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-(2-ethoxycarbonylacetyl)piperidine-1-carboxylic acid tert-butyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; Stage #3: With ammonium acetate In ethanol at 20℃; | 144.b b) 4-[5-(2-Chloro-pyridin-4-yl)-3-ethoxycarbonyl-1 H-pyrrol-2-yl]-piperidine-1 -carboxylic acid tert-butyl ester. NaH (660 mg, 14.5 mmol) is added to a solution of 4-(2-ethoxycarbonyl-acetyl)-piperidine-1- carboxylic acid tert-butyl ester in 150 ml of THF at 0 0C the mixture is allowed to react for 15 min at room temperature to give a clear solution. A solution of 3.5 g (14.9 mmol) 1-(2-chloro- pyridin-4-yl)-ethanone (free base, example 1c) in THF is added. The reaction is stirred for 1 h at 0 0C and at room temperature over night. Ice is added, followed by extraction with ethyl acetate. The combined organic layers are washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue is dissolved in 50 ml of ethanol. After adding 4.20 g(54.5 mmol) NH4OAc the reaction is stirred at room temperature over night. Ice is added, followed by extraction with ethyl acetate. The combined organic layers are washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. The crude product is purified by silica gel chromatography (hexanes-ethyl acetate gradient).1H-NMR (400 MHz, DMSO-d6): 1.27 (t, 3H), 1.47 (s, 9H), 1.75-1.81 (m, 2H), 1.90-1.97 (m,2H), 2.85-2.95 (m, 2H), 3.86 (t, 1H), 4.09-4.14 (m, 2H), 4.31 (q, 2H), 7.09 (s, 1H), 7.39 (d,1H), 7.52 (s, 1H), 8.28 (d, 1 H), 9.91 (s, 1H, NH).MS (ESI+) m/z: 434 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In ethanol for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium acetate In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 5 h / Heating 2: AlMe3; NH4Cl / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: carbethoxyacetamidine hydrochloride With sodium ethanolate In ethanol at 0℃; for 0.333333h; Stage #2: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one In ethanol at 0 - 20℃; for 16h; | 1.b b) 2-Amino-5-(2-chloro-pyridin-4-yl)-1 H-pyrrole-3-carboxylic acid ethyl ester2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (3.0 g, 12.8 mmol) is stirred in a mixture of 35 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Carbamimidoyl-acetic acid ethyl ester hydrochloride (4.26 g, 25.6 mmol) (Liebigs Ann. Chem. 1977, 1895) is suspended in 10 ml ethanol and cooled to 0 oC. To this mixture sodium ethoxide (1.74 g, 25.6 mmol) is added. The mixture is stirred for 20 minutes, then 2- bromo-1-(2-chloro-pyridin-4-yl)-ethanone in 10 ml ethanol is added dropwise. After stirring at r.t. for 16 hours the reaction is stopped by adding 100 ml water and the mixture is extracted with ethylacetate. The material obtained after removal of the solvent is used for further steps without purification.1H-NMR (400 MHZ1 DMSO-d6): 1.27 (t, 3H), 4.16 (q, 2H), 5.97 (s, 2H), 6.98 (d, 1 H), 7.44 (dd, 1H), 7.55 (d, 1 H), 8.14 (d, 1H), 11.1 (s, 1 H). MS (ESI+) m/z: 266 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; for 16h;Heating / reflux; | To a solution of <strong>[56-06-4]2,6-diamino-4-hydroxypyrimidine</strong> (269 mg, 2.1 mmol) and sodium ethoxide (159 mg, 2.3 mmol) in 8 ml ethanol is added 2-bromo-1-(2-chloro-pyridin-4-yl)-ethanone (500 mg, 2.1 mmol) (free base prepared as described in example 1 b). The mixture is heated under reflux for 16 hours and then quenched by addition of water. The white precipitate which forms is filtered and titurated with ether to give the target molecule.1H-NMR (400 MHZ, DMSO-d6): 6.34 (s, 2H), 7.17 (s, 1H), 7.65 (d, 1 H), 7.77 (s, 1 H), 8.22 (d, 1 H), 10.41 (brs, 1 H), 11.7 (brs, 1 H). MS (ESI+) m/z: 262 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In diethyl ether; water | 1.b 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (3.0 g, 12.8 mmol) is stirred in a mixture of 35 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Carbamimidoyl-acetic acid ethyl ester hydrochloride (4.26 g, 25.6 mmol) (Liebigs Ann. Chem. 1977, 1895) is suspended in 10 ml ethanol and cooled to 0 oC. To this mixture sodium ethoxide (1.74 g, 25.6 mmol) is added. The mixture is stirred for 20 minutes, then 2- bromo-1-(2-chloro-pyridin-4-yl)-ethanone in 10 ml ethanol is added dropwise. After stirring at r.t. for 16 hours the reaction is stopped by adding 100 ml water and the mixture is extracted with ethylacetate. The material obtained after removal of the solvent is used for further steps without purification.1H-NMR (400 MHZ1 DMSO-d6): 1.27 (t, 3H), 4.16 (q, 2H), 5.97 (s, 2H), 6.98 (d, 1 H), 7.44 (dd, 1H), 7.55 (d, 1 H), 8.14 (d, 1H), 11.1 (s, 1 H). MS (ESI+) m/z: 266 [MH]+ | |
With sodium hydrogencarbonate In water | 141.a a) 2-[2-(2-Chloro-pyridin-4-yl)-2-oxo-ethyl]-4-methyl-3-oxo-pentanoic acid ethyl ester. 2-Bromo-1-(2-chloro-pyridin-4-yl)-ethanone hydrobromide (500 mg) is stirred in a mixture of 20 ml aqueous NaHCO3 solution and ether to liberate the free base. The aqueous phase is extracted two more times with ether, the ether phase dried and concentrated. Ethyl isobutyrate (337 mg) in 5 ml THF is added drop wise to a solution of LiHMDS (2.1 ml 1.0 M solution) in 5 ml THF at - 78 0C. After stirring for 2 hours at -78 0C 2-bromo-1-(2- chloro-pyridin-4-yl)-ethanone (see above) dissolved in 3 ml THF is added drop wise. The reaction mixture is allowed to warm to room temperature overnight. Aqueous NH4Cl solution is added and the mixture is extracted with ethyl acetate. After removal of the solvent the title compound is obtained as a pale yellow oil. 1H-NMR (400 MHz, DMSO-d6): 1.07 (d, 3H), 1.10 (d, 3H), 1.19 (t, 3H), 2.98 (sept, 1 H), 3.50- 3.68 (m, 2H), 4.13 (q, 2H), 4.33 (t, 1H), 7.84 (d, 1H), 7.96 (s, 1H), 8.63 (d, 1H). MS (ESI+) m/z: 312 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In methanol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol for 1h; Reflux; | |
94% | Stage #1: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one; (3-methylphenyl)thiourea In ethanol for 1h; Heating; Reflux; Stage #2: With ammonia In ethanol; water at 0 - 20℃; for 1h; | 1-87 Example 1-87 4-(2-Chloro-4-pyridinyl)-7V-(3-methylphenyl)-l,3-thiazol-2-amine (150). [0359] 4-(2-Chloro-4-pyridinyl)-7V-(3-methylphenyl)-l,3-thiazol-2-amine (150). A mixture of 2-bromo-l-(2-chloro-4-pyridinyl)ethanone (0.51 g, 2.2 mmol) and 3-methylphenylthiourea (4) (0.36 g, 2.2 mmol) in EtOH (35 mL) was stirred at reflux temperature for 1 h. The mixture was cooled to 20 0C, diluted with water (80 niL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 °C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 150 (0.62 g, 94%) as a white powder: mp (EtO Ac/pet, ether) 195-197 0C; 1H NMR δ 10.30 (s, 1 H, NH), 8.45 (br d, J= 5.1 Hz, 1 H, H-6'), 7.93 (br d, J= 1.2 Hz, 1 H, H-3'), 7.87 (dd, J= 5.2, 1.4 Hz, 1 H, H-5'), 7.84 (s, 1 H, H-5), 7.55 (br d, J= 8.0 Hz, 1 H, H-6"), 7.47 (br s, 1 H, H-2"), 7.25 (br t, J= 7.8 Hz, 1 H, H-5"), 6.82 (br d, J= 7.4 Hz, 1 H, H-4"), 2.33 (s, 3 H, CH3); 13C NMR δ 163.6, 151.0 (2), 150.3, 146.2, 144.4, 140.6, 138.1, 128.8, 122.3, 119.7, 117.6, 114.2, 109.1, 21.9; MS m/z 302.5 (MH+, 100%). Anal, calcd for Ci5Hi2ClN3S: C, 59.70; H, 4.01; N, 13.92. Found: C, 59.75; H, 4.07; N, 13.82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-bromo-1-(2-chloropyridin-4-yl)ethan-1-one; 4-aminopyridine-3-carbonitrile In ethanol for 2h; Reflux; Stage #2: With sodium hydrogencarbonate In ethanol for 4h; Reflux; | 1.3 6-Aminonicotinonitnle (2 g, 16.8 mmoi) and 2-bromo-1-(2-ch]oro-4-yl)-ethanone (3.9 g, 16.8 mmol) were refluxed in ethanol (100 ml) for 2h. Pale-yellow precipitate formed. NaHC03 (2 g) was added to the cooled reaction mixture and the mixture was refluxed for another 4h. After cooling, the precipitate was filtrated, washed with water and recrystalized from ethyl acetate to give the 2-(2-chloropyridin-4-yl)-6-cyano-imidazo[1 ,2-a]pyridine (1.7 g). 1 H NMR (300 MHz, D SO~cf6) δ: 8.70 (d, 1H) 8.30 (d, 1 H) 7.63 (s, 1 H) 7.35 (d, 1H) 7.29 (d, 1 H) 7.21 (dd, 1 H) 7.14 (dd, H) ; MS (ES) miz (M+H) 255.7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C 4: sodium cyanoborohydride / acetonitrile / 15 h / 20 °C / pH 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonium acetate / ethanol 2: 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / N,N-dimethyl-formamide / Microwave irradiation 3: trifluoroacetic acid / 20 °C |
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