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CAS No. : | 659731-18-7 | MDL No. : | MFCD03095125 |
Formula : | C10H14BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OADUVPSZJLNMCG-UHFFFAOYSA-N |
M.W : | 191.04 | Pubchem ID : | 4192669 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 60.91 |
TPSA : | 43.7 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) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.44 |
Log Po/w (WLOGP) : | -0.41 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | -0.32 |
Consensus Log Po/w : | 0.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.46 mg/ml ; 0.00764 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.96 |
Solubility : | 2.08 mg/ml ; 0.0109 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.74 |
Solubility : | 3.51 mg/ml ; 0.0184 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | 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 sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 4.0h;Heating / reflux; | A mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)-benzyl]-4-methyl- l,3-oxazolidin-2-one (0.05 g, 0.084 mmol), 3-(pyrrolidmo)phenyl boronic acid (0.032 g, 0.167 mmol), tetrakis(triphenylphosphine) palladium ( 5% mol) and sodium carbonate (0.019 g, 0.18 mmol) in 7 ml of water/EtOH/toluene (1:2:4) was heated to reflux for 4 h. TLC (EtOAc:hexane /1:1) showed that the reaction was over. The solvents were removed. Water (10 ml) was added. The organic was extracted with methylene chloride (3x 10 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after flash column using EtOAc:hexane /6:4 as the eluant. LC-MS (M+l): 617.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With triethylamine;copper diacetate; In dichloromethane; for 72.0h;Molecular sieve; under air; | A mixture of 2-chloro-3-fluoro-5-hydroxypyridine (0.8 gm, 0.00544 mol), <strong>[659731-18-7]3-(1-pyrrolidinyl)phenyl boronic acid</strong> (1.03 g, 0.00544 mol), copper(II)acetate (1.08 g, 0.00544 mol), triethylamine(1.5 mL, 0.01088 mol) and powdered 4 molecular sieves in dichloromethane (20 mL) was stirred under air for 3 days. The suspension was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica eluting with ethyl acetate:hexane (3:17) to afford 2-chloro-3-fluoro-5-(3-pyrrolidin-1-ylphenoxy)pyridine as a colourless oil (0.41g, 26%).ES+ 293 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With triethylamine;copper diacetate; In dichloromethane; for 72.0h;Molecular sieve; under air; | A mixture of 2-chloro-5-hydroxypyridine (294 mg, 5.257 mol), <strong>[659731-18-7]3-(1-pyrrolidinyl)phenyl boronic acid</strong> (500 mg, 5.257 mol), copper(II)acetate (453 mg, 5.257 mol), triethylamine (5.3 mL, 26.285 mol) and powdered 4 A molecular sieves in dichloromethane (20 mL) was stirred under air for 3 days. The suspension was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica eluding with ethyl acetate:hexane (3:7) to afford 2-chloro-5-(3-pyrrolidin-1-ylphenoxy)pyridine as a colourless oil (340 mg, 24%). ES+ 275 (M+H)+ deltaH (d6-DMSO) 1.92 (4H, m) 3.20 (41-1, m) 6.20 (1H, s) 6.21 (1H, d) 6.36 (1H, d) 7.15 (1H, t) 7.43 (2H, m) 8.15 (1H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With copper diacetate; triethylamine; In dichloromethane; for 72h;Molecular sieve; Air conditions; | Intermediate 7: 2- Chloro-5- (3- (pyrrolidin- 1 -yl)phenoxy)pyrimidineA mixture of 2-chloro-5-hydroxypyrimidine (2.69g, 0.0206mol), 3-(pyrrolidin-l- yl)phenylboronic acid (3.95g, 0.0206mol), copper (II) acetate (3.75 g, 0.0206mmol), triethylamine (14.40mL, 0.0721mol) and powdered 4A molecular sieves in dichloromethane (70mL) was stirred under air for 3 days. The calcium chloride guard tube was used to protect the reaction from moisture. The suspension was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (ethyl acetate:hexane, 1: 1) to afford 2-chloro-5-(3-(pyrrolidin-l-yl)phenoxy)pyrimidine as colourless oil (1.3g, 18percent).Mass: (ES+) 275 (M+H) + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 120.0℃; for 1.5h;Microwave irradiation; | D53-chloro-N-(3-(3-(pyrrolidin-l-yl)phenyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrrolo[2,3-b]pyridin-4-yl)benzeA mixture of N-[3-bromo-l-([2-(trimethylsilyl)ethyl]oxy}methyl)- lH-pyrrolo[2,3- b]pyridin-4-yl]-3-chlorobenzenesulfonamide (D4) (233 mg, 0.451 mmol), [3-(l- pyrrolidinyl)phenyl]boronic acid (129 mg, 0.676 mmol), cesium fluoride (205 mg, 1.352 mmol) and l,r-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (36.8 mg, 0.045 mmol) in DME (5.706 mL) was heated in a microwave at 120 C for 30 minutes. Additional 3-(l-pyrrolidinyl)phenyl]boronic acid (129 mg, 0.676 mmol), cesium fluoride (68.3 mg) and l, r-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (36.8 mg, 0.045 mmol) were added into the reaction mixture and heated in a microwave at 120 C for 1 hour. The reaction mixture was partitioned between aqueous saturated NaHC03 solution and ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate (thrice). The organic extracts were combined, dried over phase separator. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane). The appropriate fractions were combined and evaporated to dryness to afford the title compound (128.1 mg). LCMS (A): m/z (M+H)+ 583, C29H35ClN403SSi requires 582 (acidic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 65.0℃; for 2.0h; | D154-bromo-l-isopropyl-3-(3-(pyrroli rolo[2,3-b]pyridine (D15)A mixture of 4-bromo-3-iodo- l-isopropyl-lH-pyrrolo[2,3-b]pyridine (D10) (2.80 g, 7.67 mmol), (3-(pyrrolidin-l-yl)phenyl)boronic acid (1.612 g, 8.44 mmol), bis(triphenylphosphine)palladium(II) chloride (0.538 g, 0.767 mmol) and 2M sodium carbonate aqueous solution (9.59 mL, 19.18 mmol) in ACN (35.0 mL) was heated at 65 C for 2 hours and then allowed to cool to RT. The mixture was evaporated to dryness and the residue partitioned between water (50 mL) and ethyl acetate (150 mL). The aqueous phase was separated and extracted with additional ethyl acetate (100 mL). The organic extracts were combined, washed with brine (50 mL), dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica eluting with cyclohexane and ethyl acetate (0-35%) to give an impure material which was further purified on silica eluting with cyclohexane and ethyl acetate (0-25%). The appropriate fractions were combined and evaporated to dryness producing the title compound (692 mg). LCMS (A): m/z (M+H)+ 384/386, C20H22BrN3 requires 383/385 (acidic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; at 65.0℃; for 1.0h; | D144-chloro-l,6-dimethyl-3-(3-(pyrro rolo[2,3-b]pyridineA mixture of 4-chloro-3-iodo- l,6-dimethyl- lH-pyrrolo[2,3-b]pyridine (D13) (500 mg, 1.631 mmol), (3-(pyrrolidin- l-yl)phenyl)boronic acid (374 mg, 1.957 mmol), bis(triphenylphosphine)palladium(II) chloride (1 14 mg, 0.163 mmol) and sodium carbonate (2M aq. solution) (8 mL, 16.00 mmol) was heated at 65 C for 1 hour. The mixture was transferred to a separatory funnel with ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (30 mL x 3). The organics were combined, dried over magnesium sulfate and concentrated. The crude was purified over normal phase chromatography eluting with ethyl acetate and cyclohexane (0-30%) to give the title compound (135 mg). LCMS (A): m/z (M+H)+ 326, C19H20C1N3 requires 325 (acidic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; for 16.0h;Inert atmosphere; Reflux; | 4-(6-Methoxy-2-methyl-4-(3-(pyrrolidin-1-yl)phenyl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole [0673] Method 42: 4-(4-chloro-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisox-azole (S13, 40 mg, 0.1 mmol, 1.0 equiv.) and <strong>[659731-18-7]3-(pyrrolidino)phenylboronic acid</strong> (70 mg, 0.3 mmol, 3.0 equiv.) were dissolved in 1,2-dimethoxyethane (4 mL). Sodium carbonate (2.0 M in water, 2 mL) was added. The system was degassed to remove oxygen and nitrogen was refilled. Pd(dppf)Cl2-CH2Cl2 (20 mg, 0.024 mmol, 0.24 equiv.) were added and the system was degassed again and refilled with nitrogen. The reaction mixture was heated at reflux for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layers were combined and concentrated on a rotary evaporator. The residue was purified by reverse HPLC to afford the title compound as a salt of CF3CO2H (30 mg, 52% yield). 1H NMR (MeOD-d4, 300 MHz): 7.59 (t, J=7.94 Hz, 1H), 7.53 (s, 1H), 7.48 (s, 1H), 7.18 (d, J=7.75 Hz, 1H), 7.10 (s, 1H), 7.00 (dd, J=8.30, 1.98 Hz, 1H), 3.67 (s, 3H), 3.50-3.35 (m, 4H), 2.95 (s, 3H), 2.30 (s, 3H), 2.12 (s, 3H), 2.12-2.20 (m, 4H). ESI-MS calculated for C27H28N5O2 [M+H]+=454.22; Observed: 454.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With bis(tri-t-butylphosphine)palladium(0); In ethanol; water; toluene; at 120.0℃; for 0.5h;Inert atmosphere; | Under argon, 78 mg (0.41 mmol) of [3-(pyrrolidin-1-yl)phenyl]boric acid, 104 mg (0.49 mmol) of potassium phosphate and 8 mg (0.016 mmol) of bis(tri-tert-butylphosphine)palladium(0) were added in succession to 60 mg (0.16 mmol) of 3-bromo-8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine (Example 21A) in a mixture of 1.2 ml of ethanol, 0.6 ml of water and 0.6 ml of toluene. The suspension was degassed with argon and then stirred at 120 C. for 30 min. After the reaction had ended, the reaction mixture was concentrated and the residue was taken up in ethyl acetate/water and extracted. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, concentrated on a rotary evaporator and dried under high vacuum. The residue was purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product fractions were combined and concentrated on a rotary evaporator. The residue was dissolved in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The combined aqueous phases were extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. This gave 32 mg of the target compound (44% of theory). LC-MS (Method 1): R=1.00 min. MS (ESpos): mlz=434 (M+H). 1H-NMR (500 Mhz, DMSO-d5) oe=1.93-2.02 (m,4H), 2.24 (s, 3H), 2.37 (s, 3H), 3.23-3.32 (m, 4H; superposed by solvent peak), 5.29 (s, 2H), 6.54 (s, 1H), 6.62 (d,1H), 6.66 (d, 1H), 6.72 (s, 1H), 7.19-7.28 (m, 2H), 7.32 (t,1H), 7.55-7.63 (m, 1H), 7.71 (s, 1H). |
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