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[ CAS No. 908142-03-0 ] {[proInfo.proName]}

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Chemical Structure| 908142-03-0
Chemical Structure| 908142-03-0
Structure of 908142-03-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 908142-03-0 ]

CAS No. :908142-03-0 MDL No. :MFCD14155851
Formula : C8H11BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :DOQUCBSZQOPLGT-UHFFFAOYSA-N
M.W : 181.98 Pubchem ID :53407782
Synonyms :

Calculated chemistry of [ 908142-03-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 48.89
TPSA : 69.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.09
Log Po/w (WLOGP) : -1.28
Log Po/w (MLOGP) : -0.52
Log Po/w (SILICOS-IT) : -0.89
Consensus Log Po/w : -0.56

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.06
Solubility : 16.0 mg/ml ; 0.0881 mol/l
Class : Very soluble
Log S (Ali) : -0.93
Solubility : 21.6 mg/ml ; 0.119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.25
Solubility : 10.4 mg/ml ; 0.0569 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 908142-03-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 908142-03-0 ]

* 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.

  • Downstream synthetic route of [ 908142-03-0 ]

[ 908142-03-0 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 1009303-42-7 ]
  • [ 908142-03-0 ]
  • [ 1009303-74-5 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 95℃; for 2h;Product distribution / selectivity; To a mixture of the appropriate chloro-substrate (1 equiv), potassium carbonate (2.5 equiv), and the appropriate boronic acid (1.1 equiv) in acetonitrile/water (1:1) (0.033 M of chloro- substrate) was added tetrakis(triphenylphosphine) palladium0 (0.05 equiv). The suspension was sonicated while degassed with nitrogen for 5 minutes then heated to 95 0C for 2 hours. Upon completion the reaction mixture was allowed to cool down to room temperature. The reaction mixture was concentrated in vacuo to half original volume. The crude residue was extracted with CH2Cl2 and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. The residue was sonicated in diethyl ether, collected by vacuum filtration to give the desired product as a yellow powder. <n="241"/>{5-[2-Chloro-4-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-2-methoxy- phenyl} -methanol: (78 % yield, 100 % purity) m/z (LC-MS, ESP): 401 [M+H]+ R/T = 3.47 min
  • 2
  • [ 938443-23-3 ]
  • [ 908142-03-0 ]
  • KU-63794 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 140℃; for 0.5h;microwave irradiation; Example 1; R7=aryl (Examples la-bx); The appropriate chloro-substrate (Inter. 7a-e)(l equiv.) was dissolved in a toluene/ethanol (1:1) solution (0.02 M). Sodium carbonate (2 equiv.) and the appropriate boronic acid (1 equiv.) were then added followed by tetrakis(triphenylphosphine) palladium (0.1 equiv). The reaction vessel was sealed and the mixture exposed to microwave radiation (140C, medium absorption setting) for 30 minutes. Upon completion the samples were filtered through a silica cartridge, washed with EtOAc and then concentrated in vacuo. The crude residue was then purified by preparative HPLC to give the compounds listed below.
  • 3
  • [ 908142-03-0 ]
  • [ 1078734-14-1 ]
  • [ 1193525-63-1 ]
  • 4
  • 3-formyl-4-methoxyphenylboronic acid [ No CAS ]
  • [ 908142-03-0 ]
  • 5
  • [ 938443-21-1 ]
  • [ 908142-03-0 ]
  • (5-(2-chloro(morpholine-4-yl)pyrido[2,3-d]pyrimidine-7-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.1% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 95℃; for 6h;Inert atmosphere; 4 - (2,7-dichloro-pyrido [2,3-d] pyrimidin-4-yl) morpholine (0.6g, 2 . 1mmol), 3 - (hydroxymethyl) - 4-methoxy phenyl boronic acid (421 mg, 2 . 3mmol)) and K 2 CO 3 (668 mg, 4 . 8mmol) soluble in CH 3 CN-H 2 O (20 ml V=2 1) in, then adding Pd (PPh 3) 4 (49 mg, 0 . 042mmol), then using N 2 system substitution reaction of 3 time, the temperature rising to 95 C reaction 6 hours later, to CH 2 Cl 2 extracting 3 times, the organic phase drying concentration, residual column chromatography to obtain product (300 mg, 37.1%).
  • 6
  • [ 908142-03-0 ]
  • 3-(2,7-dichloropyrido[2,3-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane [ No CAS ]
  • (5-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloropyrido[2,3-d]pyrimidin-7-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 18h;Reflux; 3- (2,7-dichloro-pyrido [2,3-d] pyrimidin-4-yl) -8-oxa-3-azabicyclo [3.2.1] nonane (310mg, 1mmol), 3 - hydroxymethyl-4-methoxyphenyl boronic acid (265mg, 1.45mmol), potassium carbonate (276mg, 2mmol), Pd (PPh3)4(15 mg) was dissolved in 6mL water and 30mL dioxane, the reaction was heated at reflux for 18h.Cooling to room temperature, extracted with ethyl acetate, the organic layer was dried and concentrated to give a dark brown solid, which was used without purification was used directly in the next reaction.
  • 7
  • [ 908142-03-0 ]
  • [ 87350-77-4 ]
  • C18H21NO5S [ No CAS ]
  • 8
  • [ 350595-57-2 ]
  • [ 908142-03-0 ]
  • [ 210642-96-9 ]
  • [ 287944-16-5 ]
  • (S)-(5-(7-(3,6-dihydro-2H-pyran-4-yl)-5-(3-methylmorpholino)-1,8-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
  • (S)-(5-(5-(3,6-dihydro-2H-pyran-4-yl)-7-(3-methylmorpholino)-1,8-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.8 mg; 2 mg To a solution of 5,7-dichloro-l,8-naphthyridin-2-ol (compound 1.3, 4.00 g, 18.6 mmo3) in DMA (90 mL) and water (5 mL) was added 2-(3,6-dihydro-2H-pyran-4-yl)- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane (2.80 g, 13.3 mmol), sodium carbonate (4.00 g, 37.7 mmol), [l, l'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.00 g, 2.73 mmol). The resulting mixture was stirred for 2 hours at 100 C under nitrogen. The mixture was cooled, diluted with ethyl acetate (500 mL) and washed with 10% aqueous sodium chloride (500 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (dichloromethane/methanol, 30: 1) as the eluent to obtain a mixture of compounds 27.1 and 28.1 (2.0 g) as a light yellow solid. To a solution containing a mixture of 7-chloro-5-(3,6-dihydro-2H-pyran-4-yl)-l,8-naphthyridin-2-ol (compound 27.1 ) and 5- chloro-7-(3,6-dih}'dro-2H-pyran-4-yl)-l,8-naphthyridin-2-ol (compound 28.1) (800 mg, 3.05 mmol) in 1,4- dioxane ( 10 mL) was added (2-dicyclohexylphosphino-2',6'- diisopropoxy- l, l'-bipheny])[2-(2'-amino-l, -bipheny])]palladium(II) methanesulfonate (RuPhos-Pd-G3) (254 mg, 0.30 mmol), 2-dicyclohexylphosphino-2',6'- diisopropoxybiphenyl (RuPhos)( 142 mg, 0.30 mmol), sodium ferf-butoxide (583 mg, 6.10 mmol) and (S)-3-methylmorpholine (3.1 1 g, 30.7 mmol). The resulting mixture was stirred for 2 hours at 90 C under nitrogen, then cooled. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol, 30: 1) as the eluent to obtain a mixture of compounds 27.2 and 28.2 as a light yellow solid (600 mg). A mixture of (S}-5-(3,6-dihydro-2H-pyran-4-yl)-7-(3-methylmo holino)-l ,8-naphthyridin-2-ol (compound 27.2), (5)-7-(3,6^^(Gammatheta-^-rho}7kappaiotaeta-4^1)-5-(3-eta61}etaiotaomicronphi1iotaomicron1etaomicron)-1,8- naphthyridin-2-ol (compound 28.2) (500 mg, 1 ,52 mmol) and phosphoryl chloride (30 mL) was stirred for 3 hours at 70 C. The resulting mixture was concentrated under reduced pressure. The residue was carefully quenched with water/ice (100 mL) and the resulting mixture was extracted with ethyl acetate (2 x lOOmL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Tire residue was purified by silica gel column chromatography with dichloromethane/methanol (50: 1) as the eluent to obtain a mixture of compounds 27.3 and 28.3 as a light yellow solid (350 mg). To a mixture of (5)-4-(7-chloro-4-(3,6-dihydro-2H-pyran- 4-yl)-l,8-naphthyridin-2-yl)-3-methylmo holine (compound 27.3) and (,S)~4~(7-chloro- 2-(3 ,6-dihydro-2H-pyran-4-yi)- 1 ,8-naphthyridin- -yl)-3 -etaiotaepsiloniotanuetaiotaomicronphiiotaomicronetaepsilon (compound 28.3) (90 mg, 0.26 mmol) in toluene (5 mL), ethanol (5 mL) was added (3- (hydroxymethyl)-4-metlioxyphenyl)boronic acid (60 mg, 0.33 mmol), sodium carbonate (60 mg, 0.57 mmol), and tetrakis(triphenylphosphine)pal3adiiim (80 mg, 0.07 mmol). Tire resulting mixture was stirred for 2 hours at 90 C under nitrogen . The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane/methanol (30: 1) to obtain the mixture of products. Further purified by Prep-HPLC with the following conditions was performed: Column, XBridge Prep Shield RP 18 QBD Column, 19* 150 mm, 5mu, 13 nm; mobile phase, water with 0.1% formic acid and ACN (7.0% ACN up to 25.0% in 1 min); Detector, UV 254nm. This gave (5 -(5-(7-(3,6-dihydro-2H-pyGammaan-4-yl)-5-(3-methy]mo holino)-l ,8-naphthyridin- 2-yl)-2-methoxyphenyl)methanol as a yellow solid (compound 27, 1.8 mg) and (S)-(5- (5~(3,6~dihydro~2H^yran-4-yi)-7-p-methoxyphenyl)methanol as a yellow solid ((compound 28, 2.0 mg). m/z (ES+) 448 (M+H)+ observed for both compounds.
  • 9
  • [ 908142-03-0 ]
  • (2R,2'R,6S,6'S)-4,4'-(7-chloro-1,8-naphthyridine-2,4-diyl)bis(2,6-dimethylmorpholine) [ No CAS ]
  • (5-(5,7-bis((2R,6S)-2,6-dimethylmorpholino)-1,8-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 90℃;Inert atmosphere; To a solution of (2i?,2 ?,65',6S)-4,4'-(7-chloro-l,8- eta3rhoEtanupieta6-2,4^nu1^8(2,6-etaeta6^^omicron 1iotaomicron1eta6) (compound 22.2, 105 mg, 0.27 mmol) in toluene (4 mL) and EtOH (4 mL) was added (3-(hydroxymethyl)-4- methoxyphenyl)boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium (31 mg, 0.027 mmoi) and sodium carbonate (58 mg, 0.55 mmol). The resulting mixture was stirred overnight at 90 C under nitrogen, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate to obtain impure product. The product was further purified by Prep-HPLC with the following conditions (Prep-HPLC-043): Column, XBridge Prep Shield RPI 8 OBD Column, 19* 1 0 mm, 5muetaiota, 13 nm; mobile phase, Water with 10 mmol NH4HCO3 and acetonitrile (40.0% ACN up to 56.0% in 8 min); Detector, 254 nm. This yielded compound 22 as a light yellow solid (20.7 m, 16%) . m/z (ES+) 493 (M+H)+.
  • 10
  • [ 908142-03-0 ]
  • 2,7-dichloro-4-(3,6-dihydro-2H-pyran-4-yl)-1,8-naphthyridine [ No CAS ]
  • (5-(7-chloro-4-(3,6-dihydro-2H-pyran-4-yl)-1,8-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 90℃; for 2h;Inert atmosphere; To a solution of 2,7-dichloro-4-(3,6-dihydro-2H- pyran~4-yl)~l,8~naphthyridine (compound 29.1, 100 mg, 0.36 mmol) in EtOH (5 mL) and toluene (5 mL) was added (3-(hydroxymemyl)-4-methoxyphenyl)boronic acid (65 mg, 0.36 mmol), tetrakis(triphenylphosphine)palladium (83 mg, 0.072 mmol), and sodium carbonate (76 mg, 0.72 mmol). The reaction mixture was stirred for 2 hours at 90C under nitrogen. The resulting mixture was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1 : 1) as the eiuent to obtain compound 29.2 as a yellow solid ( 120 mg, 87%).
  • 11
  • [ 908142-03-0 ]
  • 2,7-dichloro-4-(3,6-dihydro-2H-pyran-4-yl)-1,8-naphthyridine [ No CAS ]
  • (S)-(5-(4-(3,6-dihydro-2H-pyran-4-yl)-7-(3-methylmorpholino)-1,8-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
  • 12
  • [ 908142-03-0 ]
  • 2,5,7-trichloro-1,6-naphthyridine [ No CAS ]
  • (5-(5,7-dichloro-1,6-naphthyridin-2-yl)-2-methoxyphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 90℃; for 2h; To a solution of 2,5,7-trichloro-1,6-naphthyridirie(compound 32.3, 1.00 g, 4.28 mmol) in ethanol/toluene (1 : 1 (40 mL) was added sodium carbonate (910 mg, 8.59 mmol), tetrakis(triphenylphosphine)palladium (250 mg, 0.22 mmol) and <strong>[908142-03-0](3-(hydroxymethyl)-4-methoxyphenyl)boronic acid</strong> (780 mg, 4.29 mmol). The resulting mixture was stirred for 2 hours at 90 C under nitrogen. The mixture was cooled, and the precipitating solids were collected by filtration to obtain compound 32.4 as a white solid (1.0 g, 70%).
  • 13
  • [ 110-91-8 ]
  • [ 908142-03-0 ]
  • (2-methoxy-5-(morpholinosulfonyl)phenyl)methanol [ No CAS ]
  • 14
  • [ 908142-03-0 ]
  • [ 90-98-2 ]
  • C29H26O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.5 g To a 200 mL three-neck flask, under nitrogen stream, 2.0 g of 4,4?-dichlorobenzophenone, 4.4 g of <strong>[908142-03-0]3-hydroxymethyl-4-methoxyphenylboronic acid</strong>, 40 mL of 1,4-dioxane, and 40 mL of an aqueous solution of saturated sodium bicarbonate were added, and the mixture was stirred at room temperature for 30 minutes. Thereafter, 0.2 g of bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) [(AMPHOS)2PdCl2] was added, and the reaction was carried out at 90 C. for 3 hours. After confirming the progress of the reaction by thin layer chromatography (TLC), the reaction solution was cooled to room temperature, water was added, and the precipitated solid was collected by filtration. The obtained crude crystals were stirred in methanol and washed to obtain 3.5 g of an intermediate 3.
  • 15
  • [ 908142-03-0 ]
  • C29H24Br2O3 [ No CAS ]
  • 16
  • [ 908142-03-0 ]
  • C37H42O7 [ No CAS ]
  • 17
  • [ 908142-03-0 ]
  • C45H50O9 [ No CAS ]
  • 18
  • [ 908142-03-0 ]
  • C53H58O15 [ No CAS ]
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