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[ CAS No. 142569-70-8 ] {[proInfo.proName]}

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Chemical Structure| 142569-70-8
Chemical Structure| 142569-70-8
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Product Details of [ 142569-70-8 ]

CAS No. :142569-70-8 MDL No. :MFCD08460100
Formula : C29H28ClNO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 457.99 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 142569-70-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 33
Num. arom. heavy atoms : 22
Fraction Csp3 : 0.21
Num. rotatable bonds : 7
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 137.98
TPSA : 53.35 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.72
Log Po/w (XLOGP3) : 6.29
Log Po/w (WLOGP) : 6.3
Log Po/w (MLOGP) : 4.7
Log Po/w (SILICOS-IT) : 7.53
Consensus Log Po/w : 5.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.67
Solubility : 0.0000971 mg/ml ; 0.000000212 mol/l
Class : Poorly soluble
Log S (Ali) : -7.2
Solubility : 0.000029 mg/ml ; 0.0000000633 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.84
Solubility : 0.0000000665 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.81

Safety of [ 142569-70-8 ]

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

Application In Synthesis of [ 142569-70-8 ]

* 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 [ 142569-70-8 ]

[ 142569-70-8 ] Synthesis Path-Downstream   1~4

YieldReaction ConditionsOperation in experiment
89% In toluene; at 5 - 25℃; for 2.0h;Heating / reflux;Purification / work up; Example 1 - Purification of Optically Impure Compound Till) by Crystallization from Toluene[0029] A reaction vessel equipped with a thermometer, a magnetic stirrer, and a condenser was charged with compound (III) (50 g) which contained 1.1% of the (R)-compound (i.e., 97.8% ee) and toluene (250 mL). The resulting mixture was heated to reflux. After the impure compound (III) was dissolved, the resulting solution was allowed to cool to 250C, then stirred at 25C for 1 hour. Then, the solution was cooled to 5C and stirred at that temperature for 1 hour. A solid precipitated from the solution as crystals, and the resulting crystals were filtered, washed with cold toluene, then dried in vacuum at 40C for 16 hours to afford 44.5 g compound (III) (89% yield) having 99.61% (S) enantiomer and 0.39% (R)-enantiomer (99.2% ee), as measured by HPLC.Example 2 - Purification of Compound (III) by a Second Crystallization from Toluene[0030] A reaction vessel equipped with a thermometer, a magnetic stirrer, and a condenser was charged with compound (III) (44.5 g), resulting from Example 1, above, and toluene (222 mL). The resulting mixture was heated to reflux. After the compound was dissolved, the solution was allowed to cool to 25C, then stirred at 25C for 1 hour. Subsequently, the solution was cooled to 5C, then stirred at 5C for 1 hour. A solid precipitated from solution as crystals, and the resulting crystals were filtered, washed with cold toluene, and dried in vacuum at 40C for 16 hours to afford 39.6 g compound (III) (89% yield) having 99.82% (S)- enantiomer and 0.18% (R)-enantiomer (99.6% ee), as measured by HPLC.
Step 3 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0 C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4 OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2 SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound. Yield 24.06 g, 62%. 1 H NMR (CD3 COCD3) delta 1.59 (3H, s), 1.62 (3H, s), 2.11 (2H, m), 3.16 (2H, td), 4.15 (1H, s, OH), 4.52 (1H, d, OH), 4.81 (1H, m), 7.04-7.28 (3H, m), 7.37-7.57 (5H, m), 7.60 (1H, m), 7.78 (1H, s), 7.83-8.02 (4H, m), 8.32 (1H, d).
Step 3 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0 C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4 OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2 SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound. Yield 24.06 g, 62%. 1 H NMR (CD3 COCD3) delta 1.59 (3H, s), 1.62 (3H, s), 2.11 (2H, m), 3.16 (2H, td), 4.15 (1H, s, OH), 4.52 (1H, d, OH), 4.81 (1H, m), 7.04-7.28 (3H, m), 7.37-7.57 (5H, m), 7.60 (1H, m), 7.78 (1H, s), 7.83-8.02 (4H, m), 8.32 (1H, d).
Step 3. A crude solution of the title compound (the diol) in THF/toluene was concentrated from a 23.5 mg diol/mL solution to 253 mg diol/mL by distillation at atmospheric pressure (T=84-110 C.). The solution temperature was then lowered to and maintained at 50 C. Seeding at 50 C. resulted in solution of the diol seed. Hexanes (50 mL) were added dropwise over 1 hour and then the reaction was seeded again. Once again, the seed appeared to dissolve. An additional aliquot of hexanes (25 mL) was added in a dropwise manner over 15 minutes, at which point white solids began to appear in the crystallization vessel. The crystallization was aged for 10 minutes followed by the addition of hexanes (85 mL) over 30 min. The crystallization was aged at 50 C. for 30 minutes followed by the addition of hexanes (160 mL) in one portion. Following a 30 minute age, the reaction mixture was cooled to 25 C. over 60 min., and filtered. The title compound was isolated in 89 yield (99.0 analytical %, 99.6 wt % purity).

  • 2
  • [ 142569-70-8 ]
  • [ 124-63-0 ]
  • 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-methanesulfonyl-oxypropyl)phenyl)-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -15 - 60℃; for 10.25h; 100 g of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl) ethenyl) phenyl)-3- hydroxypropyl) phenyl)-2-propanol and 500 ml of toluene were charged into a round bottom flask equipped with Dean-Stark apparatus. The resultant suspension was heated to 112 0C followed by stirring for 1 hour for removal of unwanted water along with the solvent from the reaction solution. Resultant residue was cooled to about 60 C and 920 ml of acetonitrile was charged to the residue followed by further cooling to -15 C. 42.01 ml of diisopropylethylamine was added to the residue and was stirred for about 45 minutes. 16.91 ml of methanesulfonyl chloride was added drop wise to the reaction mass in 30 minutes followed by stirring for about 9 hours. Separated solid was filtered and the solid was washed with 200 ml of acetonitrile cooled to a temperature of 5 0C followed by washing with 200 ml of cyclohexane cooled to a temperature of 5 0C. The solid obtained was dried at -15 0C under vacuum for 1 hour.33.3 g of (1-mercaptomethyl) cyclopropaneacetonitrile and 500 ml of N, N- dimethylformamide were charged in another round bottom flask followed by cooling to about -15 C. 218.5 ml of n-butyl lithium in n-hexane was added drop wise to the above reaction mass in about 30 minutes under N2 atmosphere. The reaction mass was maintained at -15 0C for 45 minutes, followed by charging of the mesylated compound under N2 atmosphere. Resultant reaction mixture was stirred for 60 minutes. Reaction mass was quenched using 1000 ml of saturated sodium chloride solution (320 g sodium chloride in 1000 ml water) in 30 minutes followed by allowing the temperature of the reaction to raise to 29 C. The reaction mass was extracted with 1800 ml of toluene followed by separation of the organic layer. The total organic layer was washed with 4x1200 ml of water. The organic layer was separated and distilled completely at about 55 0C under a vacuum of 300 mm Hg to give 105.2 g of crude compound. The obtained crude and 50 ml of toluene were charged in a clean and dry round bottom flask equipped with a Dean-Stark apparatus, and was heated to 111 0C (azeotropic reflux) to remove toluene azotropically, followed by stirring the reaction mass for about 12 to 15 hrs at about 130 0C. Reaction completion was checked using thin layer chromatography. After the reaction was completed, the reaction mass was cooled to about 90 0C and the caustic lye layer was decanted. 2500 ml of preheated water (heated to 90 0C) was charged and was stirred for 1 hour for homogenous solution. pH of resultant reaction solution was adjusted to 11 by the addition of 30 ml of acetic acid under stirring. Reaction mass was washed with 4x600 ml of toluene and again pH was adjusted to 5.2 by the addition of 11.2 ml of acetic acid. Resultant reaction mass was cooled to about 28 0C and the organic and aqueous phases were separated. Aqueous layer was extracted with 2x400 ml of toluene, organic and aqueous layers were separated. The combined organic layer was washed with 5><500 ml of water. The organic layer was distilled completely at about 55 0C under a vacuum of 300 mm Hg. 100 ml of toluene was charged to the resultant residue and was stirred for 2 hours at about 28 C. The resultant homogenous solution was cooled to 2 0C for about 2 hours. Separated solid was filtered and the solid obtained was washed with 10 ml toluene cooled to a temperature of 5 0C. Solid was dried at about 70 C for 5 hours to afford 44.6 g of title compound.
  • 3
  • [ 142569-70-8 ]
  • [ 124-63-0 ]
  • [ 169954-93-2 ]
YieldReaction ConditionsOperation in experiment
81% With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -35 - -25℃; for 6.5h; Example 3 -Preparation of Montelukast Sodium from Optically Pure Compound (III)[0031] Step 1 : Preparation of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)- phenyl)-3- methanesulfonyloxy- propyl)phenyl)-2-propanol (mesylate intermediate). A reaction vessel equipped with a thermometer, a nitrogen inlet, and a magnetic stirrer was charged with a solution of compound (III), prepared as described in Example 2 (6.168 kg, 13.48 moles), in toluene (17.7 L). Acetonitrile (45.4 L) and diisopropylethylamine (2.72 L, 15.65 moles) were <n="9"/>added. The resulting solution was cooled to -25C. Mesyl chloride (1.140 L, 14.74 moles) was added dropwise over 2.5 hours, keeping the temperature at -250C. After the addition of the mesyl chloride was complete, the reaction mixture was seeded with the product and stirred at - 25C for 2 hours. The temperature was reduced to -35C over 1 hour, then the mixture was stirred for 1 hour. The product was isolated by filtration under a nitrogen blanket. The filter cake was washed with cold (-300C) acetonitrile (14 L) followed by cold (50C) hexane (16 L). After the washings, the cake was dried by passing nitrogen through the cake at 50C for 20 hours to afford 5.844 kg of the mesylate intermediate in 81% yield.
78.1% With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -35 - -25℃; for 6.5h; lOOg of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)-phenyl)-3- hydroxylpropyl)phenyl)-2-propanol (Sinochem Ningbo, China) was dissolved in a mixture of 285 ml of toluene and 712 ml of acetonitrile, and 44 ml of diisopropylethylamine was added dropwise thereto. Then, after cooling the resulting mixture to -25 C, 18.4 ml of methanesulfonylchloride was slowly added dropwise thereto, and stirred at the same temperature for 2.5 hrs. After the product was observed to form, the mixture was further stirred at -250C for 2 hrs, and then at -35 C for 2 hrs to complete the reaction. The resulting mixture was filtered under a nitrogen atmosphere at 0 C to 5 "C , and the filtrate <n="14"/>was concentrated under a reduced pressure at 0 to 5 C for 12 hrs to obtain 91 g of the title compound as a yellow solid (yield: 78.1%).1U NMR Data (300MHz, CDCl3): delta 8.1 (2H, m), 7.69 (5H, m), 7.41 (5H, m), 7.19 (3H, m), 5.70 (IH, dd), 3.25 (IH, m), 3.04 (IH, m), 2.76 (3H, s), 2.45 ( 1 H, m), 1.92 ( 1 H, s), 1.65 (6H, s).
78.1% With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -35 - -25℃; for 6.5h; Preparation Example 1 Preparation of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-methanesulfonyl-oxypropyl)phenyl)-2-propanol 100 g of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)-phenyl)-3-hydroxylpropyl)phenyl)-2-propanol (Sinochem Ningbo, China) was dissolved in a mixture of 285 ml of toluene and 712 ml of acetonitrile, and 44 ml of diisopropylethylamine was added dropwise thereto. Then, after cooling the resulting mixture to -25 C., 18.4 ml of methanesulfonylchloride was slowly added dropwise thereto, and stirred at the same temperature for 2.5 hrs. After the product was observed to form, the mixture was further stirred at -25 C. for 2 hrs, and then at -35 C. for 2 hrs to complete the reaction. The resulting mixture was filtered under a nitrogen atmosphere at 0 C. to 5 C., and the filtrate was concentrated under a reduced pressure at 0 to 5 C. for 12 hrs to obtain 91 g of the title compound as a yellow solid (yield: 78.1%). 1H NMR Data (300 MHz, CDCl3): delta 8.1 (2H, m), 7.69 (5H, m), 7.41 (5H, m), 7.19 (3H, m), 5.70 (1H, dd), 3.25 (1H, m), 3.04 (1H, m), 2.76 (3H, s), 2.45 (1H, m), 1.92 (1H, s), 1.65 (6H, s).
With triethylamine; In N,N-dimethyl-formamide; at -20 - -15℃; for 0.666667h; Stage 2.A 250 mL three-necked flask fitted with a stirrer, thermometer and dropping funnel is flushed with nitrogen. 45 g (0.0983 mol) of 2-(2-(3(S)-(3-(2-(7-chloro-2- quinolinyl)-ethenyl)phenyl)-3-(hydroxypropyl)phenyl)-2-propanol and 120 mL of N,N-dimethylformamide is poured into the flask and stirred until the diol dissolves completely. The content is cooled to between -20 and -15C in the CO2/acetone bath. After cooling 15.7 mL (11.43 g; 0.1130 mol) of triethylamine is added, the temperature is maintained at -20 to -15C and 12.38 g (8.4 mL; 0.1081 mol) of methanesulfonyl chloride is added dropwise over 40 minutes.
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -15℃;Product distribution / selectivity; REFERENCE EXAMPLE: PREPARATION OF MONTELUKAST ACID (FORMULA II).; 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3- hydroxypropyl)phenyl)-2-propanol (a diol intermediate) (140 g) and toluene (700 mL) were charged into a round bottom flask and acetonitrile (1290 mL) was charged, followed by cooling to about -15+/-2.5C. Diisopropylethylamine (69.5 mL) was charged followed by stirring for about 30 minutes. Methanesulfonyl chloride (26 mL) was added dropwise over about 30 minutes followed by stirring for about 9 hours. The formed solid was filtered and washed with acetonitrile (280 mL), followed by washing with chilled hexane (280 mL) to afford a mesylated compound of Formula III.
With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -33℃; A 1.0 L round bottom flask fitted with a mechanical stirrer, thermocouple, and addition funnel was purged with nitrogen. The flask was charged with 2-(3(S)-(3-(2-(7-Chloro-2- quinolinyl)- ethenyl) phenyl)-3-hydroxypropyl)phenyl)-2-propanol (37 gm) in toluene (96 ml) and reaction mixture was heated at 65-70C to get clear solution, followed by addition with acetonitrile (242 ml). The solution and was cooled to -33 +/- 3 0C and diisopropylethylamine (17.7 gm) was added. Then methanesulfonyl chloride (9.7 gm diluted in 37 ml acetonitrile) was added dropwise over 25-30 minutes, keeping the temp. -33 +/- 3 C. After the addition of methanesulfonyl chloride the reaction mixture was seeded with seed of the title compound (5 mg) to afford a thin slurry having solid compound was further added with acetonitrile (111 ml) and stirred at -33 +/- 3 C for 1 hour. The product was isolated by filtration of the cold suspension under a blanket of N2. The filter cake was washed with cold acetonitrile (111 ml), the cake was stored at <-10C (wet wt. = 84 gm).
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -25℃; for 1.0h;Inert atmosphere; Example 1 Preparation of 2-(2-(3(S)-(3-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3 methanesulfonyloxypropyl)phenyl-2-propanol (2) 2-(2-(3(S)-(3-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl-2-propanol (20.0 g) was dissolved in 70 ml of tetrahydrofuran, the reactor temperature was decreased to 0 C. and diisopropylethylamine (8.43 ml) was slowly added dropwise thereto. The inner temperature of the reactor was reduced to -25 C., methanesulfonyl chloride (5.54 g) was slowly added dropwise under nitrogen, and the reaction mixture was stirred at -25 C. for one hour. After completion of the reaction, 200 ml of acetonitrile was slowly added dropwise at an inner reactor temperature of -20 C. or lower. The resulting solid was filtered under nitrogen using a low-temperature filter, washed with 100 ml of acetonitrile cooled to 0 C. or lower and dried to obtain 21.7 g of the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3): delta 8.12 (m, 2H), 7.75 (m, 3H), 7.66 (d, 2H), 7.42 (m, 5H), 7.19 (m, 3H), 5.73 (dd, 1H), 3.27 (m, 1H), 3.07 (m, 1H), 2.80 (s, 3H), 2.50 (m, 1H), 2.30 (m, 1H), 1.68 (s, 6H).
With N-ethyl-N,N-diisopropylamine; In toluene; acetonitrile; at -35 - 50℃; for 3.0h;Inert atmosphere; Preparation of 2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yI) ethyl) phenyl)-3- (methanesulfony-l-oxy) methyl ethyl) phenyl)-2-propanol (mesylated mass) 2- (2-(3(S)-(3-(2-(7-chloroquinolin-2-yl) ethenyl) phenyl)-3-(hydroxypr- opyl) phenyl)-2- propanol (25gm, 0.054 mole) was dissolved in toluene (50 ml) and acetonitrile (100 ml) mixture under nitrogen atmosphere at 45-50 C temperature. Diisopropylethylamine (10.5 gm, 0.081 mole) was added to the reaction mixture and the temperature was lowered to - 35 C. to -30 C. Methane sulfonyl chloride (7.0gm, 0.060 mole) was added slowly to the reaction mixture over a period of lhr at -30C to -25C and the reaction mixture was stirred for 2 hrs to -35C to -30 C. After completion of the reaction, dimethylformamide (75ml) was added at same temperature. Further, hexane(lOOml) was added at -5C to - 10C.The organic layer was separated and 2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yl) ethenyl) phenyl)-3-(methanesulfony- loxy) methyl ethyl) phenyl)-2-propanol (mesyl derivative) in organic layer was obtained, which was further used in next step.(i.e.Step- II). Mesylated mass conversion by HPLC- 94.91%.

  • 4
  • [ 142569-70-8 ]
  • [ 2524-64-3 ]
  • 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.8% With dmap; triethylamine; In hexane; dichloromethane; ethyl acetate; toluene; Preparation Example 2 Preparation of 2-(2-(3-(S)-(3-(2-(7-chloro-2-quino-linyl)-ethenyl)phenyl)-3-diphenylphosph ate oxypropyl)phenyl)-2-propanol 20 g of 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)-phenyl)-3-hydroxypropyl)-phenyl)-2-propanol (Sinochem Ningbo, China) was dissolved in 240 ml of a mixture of methylene chloride and toluene (2:1), and 7.31 ml of triethylamine was added dropwise thereto. Then, 13.6 ml of diphenyl chlorophosphate was slowly added dropwise to the resulting mixture, followed by adding 1.06 g of 4-dimethylaminopyridine dropwise thereto. After confirming the completion of the reaction by TLC (thin layer chromatography) after 1 hr, the resulting mixture was combined with 100 ml of methylene chloride and 200 ml of distilled water, the organic layer was separated, dried over sodium sulfate, and concentrated under a reduced pressure. The residue was recrystallized using 60 ml of a mixture of ethyl acetate and n-hexane (1:3), filtered, washed with 40 ml of distilled water, and dried in warm air, to obtain 29.5 g of the title compound as a yellow solid (yield: 97.8%). M.P.: 127 C. 1H NMR (300 MHz, CDCl3): delta 8.4 (1H, d), 7.94 (1H, d), 7.75 (3H, m), 6.97-7.35 (20H, m), 5.70-5.72 (1H, m), 3.02-3.09 (2H, m), 2.29-2.34 (2H, m), 1.65 (3H, s), 1.59 (3H, s).
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