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CAS No. : | 933052-52-9 | MDL No. : | MFCD03095109 |
Formula : | C10H14BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ICRHNMKDEVGGGH-UHFFFAOYSA-N |
M.W : | 207.03 | Pubchem ID : | 4192660 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.99 |
TPSA : | 52.93 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.15 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.58 |
Log Po/w (WLOGP) : | -1.18 |
Log Po/w (MLOGP) : | -0.29 |
Log Po/w (SILICOS-IT) : | -0.68 |
Consensus Log Po/w : | -0.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 4.6 mg/ml ; 0.0222 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.26 |
Solubility : | 11.3 mg/ml ; 0.0544 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.48 |
Solubility : | 6.86 mg/ml ; 0.0331 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In butan-1-ol; at 90.0℃; for 0.166667h; | Methyl-7-bromo-3-[(2,2-dimethylpropanoyl)oxy]-4-oxo-4H-pyrido[l,2-alpha]pyrimidine-2- carboxylate, <strong>[933052-52-9](2-morpholin-4-ylphenyl)boronic acid</strong> (1.5 eqs.), palladium(II)-acetate (10 mol%), dicyclohexyl(2',6'-dirnethoxybiphenyl-2-yl)phosphine.(2.5 eqs. over catalyst), and anhydrous potassium phosphate were placed in a flask under argon and degassed n-butanol was added. The suspension was heated with stirring to 900C for 10 minutes. The mixture was diluted with dichloromethane and washed with saturated aqueous nuaetaC03. The organic phase was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was dissolved in methanol and /7-fluorobenzylamine was added (8 eqs). The mixture was stirred at 65C for 5 hours. The crude product was purified by preparative HPLC using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: Cl 8). The product was obtained after lyophilization of the pooled product fractions as bright yellow solid. EPO <DP n="47"/>IH-NMR (400 MHz, DMSO-ct°) delta: 12.23 (s, br, IH), 9.72 (t, J= 6.0, IH), 8.89 (s, IH), 8.09 (d, J = 8.0 Hz, IH), 7.57 (d, J = 8.0 Hz, IH), 7.50-7.32 (m, 4H), 7.22-7.11 (m, 4H), 4.53(d, J= 6.0, 2H), 3.52 (s, br, 4H), 2.82 (s, br, 4H). MS m/z: 475 (M+H)+. | |
With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In butan-1-ol; at 90.0℃; for 0.166667h; | Methyl-7-bromo-3-[(2,2-dimethylpropanoyl)oxy]-4-oxo-4H-pyrido[1,2-alpha]pyrimidine-2-carboxylate, <strong>[933052-52-9](2-morpholin-4-ylphenyl)boronic acid</strong> (1.5 eqs.), palladium(II)-acetate (10 mol %), dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (2.5 eqs. over catalyst), and anhydrous potassium phosphate were placed in a flask under argon and degassed n-butanol was added. The suspension was heated with stirring to 90 C. for 10 minutes. The mixture was diluted with dichloromethane and washed with saturated aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was dissolved in methanol and p-fluorobenzylamine was added (8 eqs). The mixture was stirred at 65 C. for 5 hours. The crude product was purified by preparative HPLC using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: C18). The product was obtained after lyophilization of the pooled product fractions as bright yellow solid.1H-NMR (400 MHz, DMSO-d6) delta: 12.23 (s, br, 1H), 9.72 (t, J=6.0, 1H), 8.89 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.50-7.32 (m, 4H), 7.22-7.11 (m, 4H), 4.53(d, J=6.0, 2H), 3.52 (s, br, 4H), 2.82 (s, br, 4H). MS m/z: 475 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31.5% | A mixture of N-(3-bromo-7-quinolyl)-2-methyl-pyrazole-3-carboxamide (60 mg, 172.12 mumol, 1 eq), <strong>[933052-52-9](2-morpholinophenyl)boronic acid</strong> (42.76 mg, 206.54 mumol, 1.2 eq), Cs2CO3 (168.24 mg, 516.36 mumol, 3 eq) and Pd(dppf)Cl2 (12.59 mg, 17.21 mumol, 0.1 eq) were taken up into a microwave tube in 1,4-dioxane (3 mL) and H2O (1 mL). The sealed tube was heated at 110 C. for 1 h under microwave. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (20 mL*3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to yield a residue which was purified by preparative HPLC (column: Agela DuraShell 150 mm_25 mm_5 um; mobile phase: [water (0.05% HCl)-ACN]; B %: 20%-50%, 9 min), followed by lyophilization to yield 2-methyl-N-[3-(2-morpholinophenyl)-7-quinolyl]pyrazole-3-carboxamide (28.44 mg, 54.18 mumol, 31.5% yield, 99.6% purity, 3HCl) as a yellow solid. 1H NMR (400 MHz, CD3OD) delta ppm 9.58 (d, J=1.7 Hz, 1H), 9.28 (s, 1H), 9.17 (d, J=1.7 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 8.10 (dd, J=2.0, 8.8 Hz, 1H), 7.63-7.51 (m, 3H), 7.41-7.29 (m, 2H), 7.18 (d, J=2.2 Hz, 1H), 4.24 (s, 3H), 3.66-3.57 (m, 4H), 2.96-2.86 (m, 4H); ES-LCMS m/z 414.2 [M+H]+. |
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