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CAS No. : | 387827-18-1 | MDL No. : | MFCD24465705 |
Formula : | C16H22N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HPSJZYBXANBFJH-UHFFFAOYSA-N |
M.W : | 274.36 | Pubchem ID : | 22049056 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.44 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 85.8 |
TPSA : | 55.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.34 cm/s |
Log Po/w (iLOGP) : | 3.05 |
Log Po/w (XLOGP3) : | 2.3 |
Log Po/w (WLOGP) : | 2.92 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 2.04 |
Consensus Log Po/w : | 2.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.95 |
Solubility : | 0.309 mg/ml ; 0.00113 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.1 |
Solubility : | 0.216 mg/ml ; 0.000786 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.106 mg/ml ; 0.000386 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.19 |
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 |
---|---|---|
81% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 3 h; Heating / reflux | A degassed mixture of 2.0 M aqueous [NA2CO3] solution (4.20 mL), tert-butyl [4-[(TRIFLUOROMETHYL)] sulfonyl] [OXY}-3,] 6-dihydro-1 (2H) -pyridine carboxylate (0.500 g, 1. 51 mmol), 3-aminophenylboronic acid [HEMISULFATE] (0.393 g, 2.11 mmol), lithium chloride (0.191 g, 4.50 mmol) and tetrakis-triphenylphosphine palladium (0.080 g, 0.075 mmol) in dimethoxyethane (5.00 mL) was heated at reflux temperature for 3 hours under Argon. The organic layer of the cooled reaction mixture was separated and the aqueous layer was washed with ethyl acetate (3 x 50 [ML).] The combined organic solutions were dried and concentrated in vacuo. The crude product was chromatographed (silica, hexanes: EtOAc: dichloromethane 6: 1: 1 with [1percent] isopropylamine) to give the desired product (0.330 g, [81percent). 1H] NMR (400 MHz, [CDC13)] 8 7.12 (t, [1H,] J = 7. [60] Hz), 6. [78] (d, 1H, J = 8.4 Hz), 6. [69] (t, 1H, J =. [2.] 0 Hz), 6.59 (dd, 1H, J = 2.2, 8.0 Hz), 6.01 (br, 1H), 4.10- 4.01 (d, 2H, J = 2.4 Hz), 3.61 (t, 2H, J [= 5.] 6 Hz), 2.52- 2.46 (m, 2H), 1.49 (s, 9H); ESMS m/e : 275.2 (M + H) +. Anal. Calc. for [C16H24N202] : C, 70.04 ; H, 8. [08 ;] N, 10. [21.] Found: C, 69.78 ; H, 7.80 ; N, 9.92. |
81% | With sodium carbonate In 1,2-dimethoxyethane; water for 3 h; Heating / reflux | A degassed mixture of 2.0 M aqueous Na2CO3 solution (4.20 mL), tert-butyl 4-[(trifluoromethyl) sulfonyl]oxy}-3,6-dihydro-1 (2H)-pyridine carboxylate (0.500 g, 1.51 mmol), 3-aminophenylboronic acid hemisulfate (0.393 g, 2.11 mmol), lithium chloride (0.191 g, 4.50 mmol) and tetrakis-triphenylphosphine palladium (0.080 g, 0.075 mmol) in dimethoxyethane (5.00 mL) was heated at reflux temperature for 3 hours under Argon. The organic layer of the cooled reaction mixture was separated and the aqueous layer was washed with ethyl acetate (3?50 mL). The combined organic solutions were dried and concentrated in vacuo. The crude product was chromatographed (silica, hexanes:EtOAc: dichloromethane 6:1:1 with 1percent isopropylamine) to give the desired product (0.330 g, 81percent). 1H NMR (400 MHz, CDCl3) ? 7.12 (t, 1H, J=7.60 Hz), 6.78 (d, 1H, J=8.4 Hz), 6.69 (t, 1H, J=2.0 Hz), 6.59 (dd, 1H, J=2.2, 8.0 Hz), 6.01 (br, 1H), 4.10-4.01 (d, 2H, J=2.4 Hz), 3.61 (t, 2H, J=5.6 Hz), 2.52-2.46 (m, 2H), 1.49 (s, 9H); ESMS m/e: 275.2 (M+H)+. Anal. Calc. for C16H24N2O2: C, 70.04; H, 8.08; N, 10.21. Found: C, 69.78; H, 7.80; N, 9.92. |
81% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 3 h; Heating / reflux | TERT-BUTYL 4-(3-AMINOPHENYL)-3,6-DIHYDRO-1(2H)-PYRIDINE CARBOXYLATE: A degassed mixture of 2.0 M aqueous Na2CO3 solution (4.20 mL), tert-butyl 4-[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydro-1(2H)-pyridine carboxylate (0.500 g, 1.51 mmol), 3-aminophenylboronic acid hemisulfate (0.393 g, 2.11 mmol), lithium chloride (0.191 g, 4.50 mmol) and tetrakis-triphenylphosphine palladium (0.080 g, 0.075 mmol) in dimethoxyethane (5.00 mL) was heated at reflux temperature for 3 hours under Argon. The organic layer of the cooled reaction mixture was separated and the aqueous layer was washed with ethyl acetate (3*50 mL). The combined organic solutions were dried and concentrated in vacuo. The crude product was chromatographed (silica, hexanes:EtOAc:dichloromethane 6:1:1 with 1percent isopropylamine) to give the desired product (0.330 g, 81percent). 1H NMR (400 MHz, CDCl3) δ 7.12 (t, 1H, J=7.60 Hz), 6.78 (d, 1H, J=8.4 Hz), 6.69 (t, 1H, J=2.0 Hz), 6.59 (dd, 1H, J=2.2, 8.0 Hz), 6.01 (br, 1H), 4.10-4.01 (d, 2H, J=2.4 Hz) 3.61 (t, 2H, J=5.6 Hz), 2.52-2.46 (m, 2H), 1.49 (s, 9H); ESMS m/e: 275.2 (M+H)+. Anal. Calc. for C16H24N2O2: C, 70.04; H, 8.08; N, 10.21. Found: C, 69.78; H, 7.80; N, 9.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water at 100℃; | A mixture of 2 M AQ NA2C03 solution (42 mL), triflate from Step 1 (50.0 g, 15.1 mmol), 3- aminophenylboronic acid hemisulfate (3.93 g, 2.11 MMOL), lithium chloride (1.91 g, 45.0 mmol), and tetrakis-triphenyl phosphine palladium (0.80 g, 0.75 mmol) in dimethoxyethane (50 mL) was purged with argon and heated at 100°C under an inert atmosphere overnight. The organic layer of the cooled reaction mixture was separated, and the aqueous layer was washed with EtOAc (3x). The combined organic extracts were dried and concentrated in vacuo. The crude product was separated by flash chromatography (silica, EtOAc: Hexane 3: 7) to give the product as a yellow oil (2.5 g, 60 percent). 1H NMR (CDC13) 6 7.25 (s, 1 H), 7.22 (m, 1H), 6.92 (m, 2 H), 6.84 (m, 1H), 6.02 (s, 1H), 4.1 (m, 2H), 3.62 (2 H), 2.49 (s, 2H), 1.49 (s, 9H), 1.26 (t, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 3 h; Heating / reflux | A mixture of 2 M aqueous Na2CO3 solution (4.2 mL), tert-butyl 4-[(trifluoromethyl)sulfonyl]oxy}-1,2,3,6-tetrahydro-1-pyridine-carboxylate (0.500 g, 1.51 mmol), 3-aminophenylboronic acid hemisulfate (0.393 g, 2.11 mmol), lithium chloride (0.191 g, 4.50 mmol) and tetrakis-triphenylphosphine palladium(0) (0.080 g, 0.075 mmol) in dimethoxyethane (5 mL) was heated at reflux temperature for 3 hours, under an inert atmosphere (an initial degassing of the mixture is recommended to prevent the formation of triphenylphosphine oxide). The organic layer of the cooled reaction mixture was separated and the aqueous layer was washed with ethyl acetate (3.x.). The combined organic extracts were dried and concentrated in vacuo. The crude product was chromatographed (silica, hexanes:EtOAc:dichloromethane (6:1:1) with 1percent added isopropylamine to protect the BOC group from hydrolysis) to give 0.330 g of the desired product in 81percent yield. 1H NMR (400 MHz, CDCl3) δ 7.12 (t, 1H, J=7.60 Hz), 6.78 (d, 1H, J=8.4 Hz), 6.69 (t, 1H, J=2.0 Hz), 6.59 (dd, 1H, J=2.2, 8.0 Hz), 6.01 (m, 1H), 4.10-4.01 (d, 2H, J=2.4 Hz), 3.61 (t, 2H, J=5.6 Hz), 2.52-2.46 (m, 2H), 1.49 (s, 9H); ESMS m/e: 275.2 (M+H)+. Anal. Calc. for C16H24N2O2: C, 70.04; H, 8.08; N, 10.21. Found: C, 69.78; H, 7.80; N, 9.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With hydrogen In ethanol at 20℃; for 48 h; | A mixture of tert-butyl [4- (3-AMINOPHENYL)-3,] 6-dihydro- [1] [(2H)-PYRIDINECARBOXYLATE] (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 [ML)] was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane: methanol: isopropylamine 95: 5: 1) to give the desired product (2.63 g, [84percent). 1H] NMR (400 MHz, [CDC13)] [8] 7.10 (t, 1H, J = 7.6 [HZ),] 6.62 (d, 1H, J [=] 8.4 Hz), 6.60-6. 59 (m, 2H), 4.27-4. 18 (m, 2H), 3.62-3. 58 (m, 2H), 2.80-2. 72 (m, 2H), 2.62-2. 59 (m, 1H), 1.89-1. 52 (m, 4H), 1.49 (s, 9H); ESMS m/e: [277.] 2 (M + H) [+.] |
84% | With hydrogen In ethanol at 20℃; for 48 h; | A mixture of 3.10 g of tert-butyl 4-(3-aminophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (11.3 mmol) and 1.0 g of 10percent Pd/C in 200 mL of ethanol was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:methanol 95:5 with 1percent isopropylamine added to protect the BOC group from hydrolysis) to give 2.63 g of the desired product (84percent). 1H NMR (400 MHz, CDCl3) δ 7.10 (t, 1H, J=7.60 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+. |
84% | With hydrogen In ethanol at 20℃; for 48 h; | A mixture of tert-butyl 4-(3-aminophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 mL) was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:methanol:isopropylamine 95:5:1) to give the desired product (2.63 g, 84percent). 1H NMR (400 MHz, CDCl3) ? 7.10 (t, 1H, J=7.6 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+. |
84% | With hydrogen In ethanol at 20℃; for 48 h; | TERT-BUTYL 4-[3-(AMINO)PHENYL]-1-PIPERIDINECARBOXYLATE: A mixture of tert-butyl 4-(3-aminophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 mL) was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane: methanol:isopropylamine 95:5:1) to give the desired product (2.63 g, 84percent). 1H NMR (400 MHz, CDCl3) δ 7.10 (t, 1H, J=7.6 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+. |
63% | With hydrogen In ethanol at 20℃; for 48 h; | A mixture OF TERT-BUTYL 4- (3-AMINOPHENYL)-3, 6-DIHYDRO-1 (2H) -pyridinecarboxylate (3.30 g, 12.03 mmol) and 1.0 g of 10percent Pd/C in 200 mL ethanol was hydrogenated at rt for 2 days. The reaction mixture was filtered and washed with ethanol. The combined ethanol extracts were concentrated in vacuo to afford the desired product (2.1 g, 63percent). LC-MS M+H 276.7, RT 2. 0.5 1H NMR (DMSO): 6 6.9 (s, 1H), 6.4 (m, 3H), 4.9 (s, 2H), 4.0 (m, 2H), 2.7 (m, 2H), 1.7 (d, 2H), 1.4 (s, 9H). |
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