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158966-92-8

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  • Cyclopropaneaceticacid,1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]- 158966-92-8

    Cas No: 158966-92-8

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158966-92-8 Usage

Originator

Singulair,Merck Pharmaceutical,Canada

Uses

cardiostimulant,

Therapeutic Function

Anti-asthmatic

Mechanism of action

Montelukast was developed from other weakly antagonistic quinoline derivatives. A number of changes can be made to the structure without the loss of activity. These include changing the double bond between the two aromatic rings to an ether linkage, reducing the quinoline ring, changing the chlorine to a fluorine, and/or exchanging the sulfur for an amide group.

Pharmacokinetics

Montelukast is a high-affinity, selective antagonist of the cysLT1 receptor. It is rapidly absorbed orally, with a bioavailability of 64%. Montelukast is 99% bound to plasma proteins and is extensively metabolized in the liver by CYP3A4 and CYP2C9 to oxidated products. CYP3A4 oxidizes the sulfur and the C-21 benzylic carbon, whereas CYP2C9 is selectively responsible for the methyl hydroxylation.

Clinical Use

Leukotriene receptor antagonist: Prophylaxis of asthma Seasonal allergic rhinitis

Side effects

Montelukast did not demonstrate any significant adverse effects greater than placebo in clinical trials; however, because it is metabolized by the cytochrome P450 (CYP450) enzymes, its plasma levels should be monitored when coadministered with CYP450-inducing drugs, such as phenobarbital, rifampin, and phenytoin.

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Extensively metabolised in the liver by cytochrome P450 isoenzymes CYP3A4, CYP2A6, and CYP2C9. Excreted principally in the faeces via the bile. Metabolites have minimal therapeutic activity.

Check Digit Verification of cas no

The CAS Registry Mumber 158966-92-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,9,6 and 6 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 158966-92:
(8*1)+(7*5)+(6*8)+(5*9)+(4*6)+(3*6)+(2*9)+(1*2)=198
198 % 10 = 8
So 158966-92-8 is a valid CAS Registry Number.
InChI:InChI=1/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/t32-/m1/s1

158966-92-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name montelukast

1.2 Other means of identification

Product number -
Other names UNII-MHM278SD3E

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:158966-92-8 SDS

158966-92-8Synthetic route

1-(mercaptomethyl)cyclopropane acetic acid disodium salt

1-(mercaptomethyl)cyclopropane acetic acid disodium salt

C35H31ClNO5P

C35H31ClNO5P

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 1-(mercaptomethyl)cyclopropane acetic acid disodium salt; C35H31ClNO5P With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5 - 20℃; Inert atmosphere;
Stage #2: With acetic acid In tetrahydrofuran at -5 - 0℃; pH=2 - 3;
98.7%
montransluconate p-aminoacetanilide

montransluconate p-aminoacetanilide

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In dichloromethane; water for 0.25h;98.2%
[R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid
851755-56-1

[R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid

methylmagnesium chloride
676-58-4

methylmagnesium chloride

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With cerium chloride In tetrahydrofuran at -5 - 65℃; for 3.5h; Inert atmosphere;98%
With cerium(III) chloride In tetrahydrofuran at -5 - 65℃; Product distribution / selectivity; Inert atmosphere;52.3%
In tetrahydrofuran; toluene at 0 - 5℃;
Stage #1: With cerium(III) chloride In tetrahydrofuran at -65 - 20℃; for 3h; Heating / reflux;
Stage #2: methylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 3h;
Stage #3: [R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid With water; acetic acid Product distribution / selectivity; more than 3 stages;
Stage #1: methylmagnesium chloride With cerium(III) chloride In tetrahydrofuran at -5 - 0℃; Inert atmosphere;
Stage #2: [R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid In tetrahydrofuran at -5 - 0℃; Inert atmosphere;
(1-[(1(R)-(3-((E)-2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-3-(2-(1-tetrahydropyran-2-yloxy-1-methylethyl)phenyl)propyl)thiomethyl]cyclopropyl)acetic acid adamantylamine salt
950665-85-7

(1-[(1(R)-(3-((E)-2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-3-(2-(1-tetrahydropyran-2-yloxy-1-methylethyl)phenyl)propyl)thiomethyl]cyclopropyl)acetic acid adamantylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20℃; for 0.5h;98%
With acetic acid Product distribution / selectivity;
1-(((1-(R)-(3-(2-(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl) thio)methyl)cyclopropaneacetic acid dipropylamine salt
880769-26-6

1-(((1-(R)-(3-(2-(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl) thio)methyl)cyclopropaneacetic acid dipropylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In water; isopropyl alcohol at 4 - 40℃; for 17h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;98%
With acetic acid In dichloromethane; water at 25 - 35℃; Product distribution / selectivity;70.3%
2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester
152922-73-1

2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester

2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol
807638-71-7

2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Inert atmosphere;97.92%
Stage #1: 2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester; 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol With sodium methylate In dimethyl sulfoxide at -5 - 0℃; for 10h;
Stage #2: With water; acetic acid at 10 - 20℃; pH=6.6; Product distribution / selectivity;
Stage #1: 2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester; 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol With sodium hydroxide In ISOPROPYLAMIDE; water at -6 - 38℃;
Stage #2: With tartaric acid In tetrahydrofuran; water pH=3 - 5;
Montelukast sodium
151767-02-1

Montelukast sodium

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 25℃; for 1h;97%
With hydrogenchloride In water at 20℃; for 1h; pH=6;97.9%
With hydrogenchloride; citric buffer In water; acetone at 20 - 25℃; for 2h;76%
1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetic acid L-(+)-α-phenylglycinol salt
1005743-16-7

1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetic acid L-(+)-α-phenylglycinol salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With water; acetic acid In toluene at 35℃; for 0.5h; pH=< 6; Product distribution / selectivity;97%
1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt
577953-88-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In water; isopropyl alcohol at 4 - 40℃; for 17h; Inert atmosphere;97%
With acetic acid In water; toluene Product distribution / selectivity;86.39%
With acetic acid In water; toluene Product distribution / selectivity;86.39%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

C39H34ClNO4S

C39H34ClNO4S

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: methyl magnesium iodide With lanthanum(III) chloride; lithium chloride In toluene at 0℃; for 2h; Inert atmosphere;
Stage #2: C39H34ClNO4S In tetrahydrofuran; toluene at 0℃; for 3h; Inert atmosphere;
94%
2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol

2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol

1-(sulfanylmethyl)cyclopropaneacetic acid
162515-68-6

1-(sulfanylmethyl)cyclopropaneacetic acid

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 1-(sulfanylmethyl)cyclopropaneacetic acid With 3-ethyl-1-methyl-1H-imidazol-3-ium bromide In dimethyl sulfoxide at 10℃; for 0.0833333h;
Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 10℃; for 0.166667h;
Stage #3: 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-diphenylphosphatoxypropyl)phenyl)-2-propanol In dimethyl sulfoxide at 15 - 17℃; for 1h; Product distribution / selectivity;
93%
C36H36ClNO4S

C36H36ClNO4S

methylmagnesium chloride
676-58-4

methylmagnesium chloride

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride With zinc(II) chloride In tetrahydrofuran; 2-methyl-propan-1-ol at 5℃; for 0.666667h; Inert atmosphere;
Stage #2: C36H36ClNO4S In tetrahydrofuran for 4h; Inert atmosphere;
92%
2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile
866923-62-8

2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile With sodium hydroxide; ethanol; water for 15h; Heating / reflux;
Stage #2: With acetic acid In ethanol; water; toluene Product distribution / selectivity;
91%
Stage #1: 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile With sodium hydroxide; ethanol; water for 30h; Heating / reflux;
Stage #2: With water; acetic acid In toluene for 0.5h; pH=5.6; Product distribution / selectivity;
86%
Stage #1: 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile With sodium hydroxide; water; tetrabutylammomium bromide In toluene at 120℃; for 168h;
Stage #2: With acetic acid In water; toluene Product distribution / selectivity;
83%
1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid methyl ester
855473-51-7

1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid methyl ester

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; methanol at 10 - 20℃; Product distribution / selectivity;90.2%
With methanol; sodium hydroxide In tetrahydrofuran for 5h;66%
Stage #1: 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid methyl ester With methanol; sodium hydroxide; water In tetrahydrofuran at 0 - 20℃; for 48h;
Stage #2: With water; ammonium chloride; acetic acid In tetrahydrofuran pH=5; Product distribution / selectivity;
65.57%
sodium 1-(mercaptomethyl)-cyclopropane acetate
952585-15-8

sodium 1-(mercaptomethyl)-cyclopropane acetate

C36H34ClNO4S

C36H34ClNO4S

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
at 10 - 20℃; for 10h; Concentration;90.2%
C35H36ClNO3S*H3N
1124196-02-6

C35H36ClNO3S*H3N

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In water at 25 - 30℃; for 5 - 6h; Product distribution / selectivity;90%
With toluene at 50 - 60℃; for 6h; Product distribution / selectivity;
[R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl) ethenyl]phenyl]-3-[2-(methylcarbonyl)phenyl] propyl]thio]methyl]cyclopropane acetic acid
937275-23-5

[R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl) ethenyl]phenyl]-3-[2-(methylcarbonyl)phenyl] propyl]thio]methyl]cyclopropane acetic acid

methylmagnesium bromide
75-16-1

methylmagnesium bromide

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: methylmagnesium bromide With lithium chloride In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere;
Stage #2: [R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl) ethenyl]phenyl]-3-[2-(methylcarbonyl)phenyl] propyl]thio]methyl]cyclopropane acetic acid In tetrahydrofuran for 5h; Inert atmosphere;
90%
1-(mercaptomethyl)cyclopropanylacetic acid

1-(mercaptomethyl)cyclopropanylacetic acid

2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)-phenyl)-3-diphenylphosphate oxypropyl)phenyl)-2-propanol
1141487-07-1

2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)-phenyl)-3-diphenylphosphate oxypropyl)phenyl)-2-propanol

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 1-(mercaptomethyl)cyclopropanylacetic acid; 2-(2-(3-(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)-phenyl)-3-diphenylphosphate oxypropyl)phenyl)-2-propanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 18 - 20h;
Stage #2: With ammonium chloride In water; N,N-dimethyl-formamide at 20℃; Product distribution / selectivity;
87.1%
(1-{1-(R)-(3-bromophenyl)-3-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid
1015076-80-8

(1-{1-(R)-(3-bromophenyl)-3-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid

7-chloro-2-ethenylquinoline
177748-00-4

7-chloro-2-ethenylquinoline

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4.25h;85%
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4h; Product distribution / selectivity; Heck Reaction;67.6%
Stage #1: (1-{1-(R)-(3-bromophenyl)-3-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid; 7-chloro-2-ethenylquinoline With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4h;
Stage #2: With water; citric acid In ethyl acetate; N,N-dimethyl-formamide; toluene pH=3 - 4;
Stage #1: (1-{1-(R)-(3-bromophenyl)-3-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid; 7-chloro-2-ethenylquinoline; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide for 0.25h;
Stage #2: With triethylamine In N,N-dimethyl-formamide at 100℃; for 4h;
Stage #3: With citric acid In water; ethyl acetate; N,N-dimethyl-formamide; toluene pH=3 - 4;
C6H8N2*C35H36ClNO3S
1124196-05-9

C6H8N2*C35H36ClNO3S

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In toluene at 25 - 30℃; for 12 - 14h;85%
C35H34ClNO4S

C35H34ClNO4S

methylmagnesium bromide
75-16-1

methylmagnesium bromide

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
In toluene at -10 - -5℃; for 5h; Inert atmosphere;85%
1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-((1-tetrahydropyranyloxy)-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropyl acetate
1000788-70-4

1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-((1-tetrahydropyranyloxy)-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropyl acetate

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-((1-tetrahydropyranyloxy)-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropyl acetate With pyridine; toluene-4-sulfonic acid In methanol at 60℃; for 8h;
Stage #2: With sodium hydroxide In methanol at 30℃; for 2h;
84.9%
2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester
152922-73-1

2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester

2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(methanesulfonyl-1-oxy)methylethyl)phenyl)-2-propanol
169954-93-2

2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(methanesulfonyl-1-oxy)methylethyl)phenyl)-2-propanol

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester With sodium hexamethyldisilazane In tetrahydrofuran at -15℃; for 1h; Inert atmosphere;
Stage #2: 2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(methanesulfonyl-1-oxy)methylethyl)phenyl)-2-propanol In tetrahydrofuran at -15℃; for 7h; Product distribution / selectivity; Inert atmosphere;
84.7%
1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt
1100021-03-1

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In toluene at 25 - 30℃; for 12 - 14h;81%
C34H32ClNO4S*ClH

C34H32ClNO4S*ClH

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride With cerium(III) chloride In tetrahydrofuran at 0 - 5℃; for 1.16667h;
Stage #2: C34H32ClNO4S*ClH In tetrahydrofuran at 10℃; for 0.166667h;
Stage #3: With water; sodium acetate; acetic acid In tetrahydrofuran Product distribution / selectivity;
80%
C34H32ClNO4S*ClH

C34H32ClNO4S*ClH

methylmagnesium chloride
676-58-4

methylmagnesium chloride

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride; cerium(III) chloride In tetrahydrofuran at 0 - 5℃; for 1.16667h;
Stage #2: C34H32ClNO4S*ClH In tetrahydrofuran at 10℃; for 0.166667h;
80%
1-(mercaptomethyl)-cyclopropaneacetic acid
169954-92-1

1-(mercaptomethyl)-cyclopropaneacetic acid

2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol
807638-71-7

2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
Stage #1: 1-(mercaptomethyl)-cyclopropaneacetic acid; 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol With sodium hydroxide In N,N-dimethyl-formamide at -5 - 0℃; for 6h;
Stage #2: With water; sodium chloride In Isopropyl acetate; N,N-dimethyl-formamide for 0.5h;
Stage #3: With tartaric acid In water Product distribution / selectivity;
71.1%
Stage #1: 1-(mercaptomethyl)-cyclopropaneacetic acid; 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol With sodium hydroxide In N,N-dimethyl-formamide at -5 - 0℃; for 6h;
Stage #2: With water; sodium chloride In Isopropyl acetate; N,N-dimethyl-formamide for 0.583333h;
Stage #3: With tartaric acid In Isopropyl acetate; water at 0 - 20℃; for 4.25h; pH=4 - 5; Product distribution / selectivity;
42.54%
Stage #1: 1-(mercaptomethyl)-cyclopropaneacetic acid; 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol With sodium hydroxide In N,N-dimethyl-formamide at -5 - 0℃; for 6h;
Stage #2: With water; sodium chloride In Isopropyl acetate; N,N-dimethyl-formamide for 0.75h;
Stage #3: With pyrographite; tartaric acid Product distribution / selectivity; more than 3 stages;
montelukast isopropylamine salt
918972-53-9

montelukast isopropylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In dichloromethane; water at 25 - 35℃; for 0.5h;70.3%
With acetic acid In dichloromethane; water at 25 - 35℃; for 0.5h; pH=4.5;70.3%
With acetic acid In dichloromethane; water for 0.166667h; pH=4.0 - 4.5; Product distribution / selectivity;
1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt
880769-29-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt

montelukast
158966-92-8

montelukast

Conditions
ConditionsYield
With acetic acid In dichloromethane; water at 20 - 25℃; Product distribution / selectivity; Heating / reflux;70.3%
sodium hydroxide
1310-73-2

sodium hydroxide

montelukast
158966-92-8

montelukast

Montelukast sodium
151767-02-1

Montelukast sodium

Conditions
ConditionsYield
In methanol; toluene at 20℃; for 1h; Product distribution / selectivity;100%
In methanol; toluene at 2 - 20℃; for 0.75h; Product distribution / selectivity;100%
In methanol at 20℃; for 1h; Product distribution / selectivity;73%
In methanol at 25 - 35℃; for 0.166667h;
montelukast
158966-92-8

montelukast

Montelukast sodium
151767-02-1

Montelukast sodium

Conditions
ConditionsYield
With sodium hydroxide In methanol; toluene at 20℃; for 1h;100%
With sodium hydroxide In methanol; water; toluene for 0.5h; Product distribution / selectivity; Alkaline aqueous solution;98%
With sodium hydroxide In methanol at -5 - 35℃; for 1h;98.7%
montelukast
158966-92-8

montelukast

C35H36ClNO3S*H3N
1124196-02-6

C35H36ClNO3S*H3N

Conditions
ConditionsYield
With ammonia In ethyl acetate at 20 - 25℃; for 1h;97%
Cyclopentamine
1003-03-8

Cyclopentamine

montelukast
158966-92-8

montelukast

montelukast cyclopentylammonium
947373-22-0

montelukast cyclopentylammonium

Conditions
ConditionsYield
In acetonitrile at 25℃; for 1h; Heating / reflux;95%
cycloheptanamine
5452-35-7

cycloheptanamine

montelukast
158966-92-8

montelukast

(R-(E))-1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid cycloheptylammonium salt
947370-32-3

(R-(E))-1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid cycloheptylammonium salt

Conditions
ConditionsYield
In ethyl acetate at 25 - 60℃; for 1h;95%
In ethyl acetate65%
In ethyl acetate at 25℃; Product distribution / selectivity;
In ethyl acetate at 20℃;
Cyclododecylamine
1502-03-0

Cyclododecylamine

montelukast
158966-92-8

montelukast

C12H25N*C35H36ClNO3S

C12H25N*C35H36ClNO3S

Conditions
ConditionsYield
In cyclohexane; toluene at 25℃; for 1h; Heating / reflux;95%
benzylamine
100-46-9

benzylamine

montelukast
158966-92-8

montelukast

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt
1100021-03-1

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt

Conditions
ConditionsYield
In ethyl acetate at 20 - 25℃; for 1h;95%
In n-heptane; ethyl acetate at 20 - 25℃; for 50h;
In ethyl acetate at 20℃; for 24h;
propylamine
107-10-8

propylamine

montelukast
158966-92-8

montelukast

montelukast n-propylamine salt
1100021-00-8

montelukast n-propylamine salt

Conditions
ConditionsYield
In n-heptane; toluene; acetonitrile95%
2-aminobutanol
96-20-8, 13054-87-0

2-aminobutanol

montelukast
158966-92-8

montelukast

1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate 2-amino-1-butanol

1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate 2-amino-1-butanol

Conditions
ConditionsYield
In ethyl acetate at 15 - 25℃; for 5h; Time; Solvent; Temperature;95%
cyclooctylamine
5452-37-9

cyclooctylamine

montelukast
158966-92-8

montelukast

(R-(E))-1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid cyclooctylammonium salt
947370-34-5

(R-(E))-1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid cyclooctylammonium salt

Conditions
ConditionsYield
In toluene at 25℃; for 1h; Heating / reflux;94%
In ethyl acetate Product distribution / selectivity;70%
In water; toluene for 1.5h; Product distribution / selectivity;70%
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

montelukast
158966-92-8

montelukast

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt
577953-88-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

Conditions
ConditionsYield
In n-heptane; toluene Product distribution / selectivity;90%
In ethyl acetate; toluene Product distribution / selectivity;61%
In toluene at 20 - 25℃; for 0.25h; Product distribution / selectivity;59.67%

158966-92-8Upstream product

158966-92-8Downstream Products

158966-92-8Relevant articles and documents

Montelukast sodium intermediate compound

-

Paragraph 0066; 0067, (2020/12/08)

The invention provides a novel montelukast sodium intermediate compound and a preparation method thereof. The intermediate compound is good in stability and convenient to store; the intermediate compound serves as a starting material of montelukast sodium, the synthesized montelukast sodium is high in yield and good in purity; and the structural formula of the intermediate compound is shown in thespecification,

Montelukast sodium intermediate and preparation method and application thereof

-

Paragraph 0101; 0102; 0103, (2017/08/31)

The invention relates to a series of novel compounds as shown in a formula (III) and a preparation method thereof. The invention also relates to an application of the novel compounds as shown in the formula (III) in synthesizing Montelukast sodium. The compounds as shown in the formula (III) are critical intermediates in the Montelukast sodium synthesizing process, and play a critical role of synthesizing the final target compound. The intermediate is stable in chemical property, the preparation process is mild in reaction condition, the yield is high, the optical purity is high, and the intermediate is suitable for large-scaled production. The formula is as shown in the description.

Preparation method of montelukast sodium intermediates

-

Paragraph 0031; 0032; 0033, (2016/12/26)

The invention relates to a preparation method of montelukast sodium intermediates. The method comprises the steps that under the protection of inert gas, in solvent, nucleophilic substitution is conducted on a montelukast mother nucleus compound, replaced by various leaving groups, of secondary hydroxyl and various side chains respectively under the action of a catalyst, and various montelukast sodium intermediates are obtained. According to the preparation method of the montelukast sodium intermediates, new catalysts of 4-dimethylaminopyridine and 4-pyrrolidinopyridine are utilized, the reaction is mild in condition and rapid, the product is single, purification is easy and convenient, the obtained intermediates are high in optical purity and higher in yield, and the preparation method is more suitable for industrial production.

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