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834153-87-6

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Basic Information
CAS No.: 834153-87-6
Name: elagolix
Article Data: 9
Molecular Structure:
Molecular Structure of 834153-87-6 (elagolix)
Formula: C32H30 F5 N3 O5
Molecular Weight: 631.599
Synonyms: Elagolix;NBI 56418;
Density: 1.350
Boiling Point: 728.6±70.0 °C(Predicted)
PSA: 102.56000
LogP: 5.92590
Related products
Synthetic route
832720-84-0

4-((R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-trifluoromethylbenzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-yl]-1-phenylethylamino)butyric acid ethyl ester

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Stage #1: ethyl (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoate With sodium hydroxide; water In ethanol at 35℃; for 2h;
Stage #2: With hydrogenchloride In water at 10 - 22℃; for 17h; pH=6.1;		91%
With water; sodium hydroxide In ethanol at 35℃;86%
With water; sodium hydroxide In ethanol at 50℃; for 2h;83.59%

(R)-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2-(2-oxopyrrolidin-1-yl)-2-phenylethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 55 - 60℃;89%

ethyl (R)-4-((tert-butoxycarbonyl)(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1-(2H)-yl)-1-phenylethyl)amino)butyrate

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; potassium carbonate In tetrahydrofuran at 50℃; for 6h; Solvent; Temperature;82%
830346-50-4

3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate

692-29-5

Succinic semialdehyde

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 25℃; for 18h; Reagent/catalyst; Solvent; Temperature;65%
1092070-97-7

methyl (R)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-[2-fluoro-6-(trifluoromethyl)benzyl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyrate

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 45℃;
830346-50-4

3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
2: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
2: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
2: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
1150560-59-0

5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 55 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
3: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
3: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
3: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
1150560-54-5

1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate / acetone; water / 0.83 h / 15 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 55 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
4: sodium hydroxide; water / ethanol / 35 °C
View Scheme
352303-67-4

(2-fluoro-3-methoxyphenyl)boronic acid

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate / acetone; water / 0.83 h / 15 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 55 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
4: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
110143-62-9

(S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester

834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 55 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
3: sodium hydroxide; water / ethanol / 35 °C
View Scheme
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Specification

Elagolix , with the CAS register number 834153-87-6, has the chemical molecular formular C32H30F5N3O5. And it can also be called as 4-[[(1R)-2-[5-(2-Fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]amino]butanoic acid , and NBI 56418 .

Some characteristics of Elagolix are as below: (1)molecular weight:631.59 ; (2)Density: 1.350 .

Elagolix is a kind of new chemical entity which is being a first-in-class oral gonadotropin-realeasing hormone( GnTh) antagonist. It allows partial estrogen and belongs to the BNF category of posterior pituitary hormones and antagonists (06.05.02). For now, it is being used as the experimental drug in the treatment endometriosis pain. And some reaserch will study this kind of chemical as the curing medicine for the uterine leiomyoma.

As for the market condition of this kind of chemical, it has many suppliers in China, such as Hangzhou Onicon Chemical Co., Ltd., MedKoo Biosciences , and Shanghai Sun-shine Chemical Technology Co., Ltd.