EPZ011969

Base Information

• Chemical Name: EPZ011969
• CAS No.: 1598383-40-4
• Molecular Formula: C35H51N5O4
• Molecular Weight: 605.821
• Mol file: 1598383-40-4.mol

Synonyms:EPZ011969;EPZ011989;N-[(1,2-Dihydro-4,6-dimethyl-2-oxo-3-pyridinyl)methyl]-3-[ethyl[trans-4-[(2-methoxyethyl)methylamino]cyclohexyl]amino]-2-methyl-5-[3-(4-morpholinyl)-1-propyn-1-yl]benzamide

Chemical Property of EPZ011969

Chemical Property:

• Boiling Point: 756.7±60.0 °C(Predicted)
• PKA: 11.88±0.10(Predicted)
• PSA: 90.14000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 3.95830

Purity/Quality:

99%, ^*data from raw suppliers

EPZ011989 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The lysine methyltransferase EZH2 (KMT6), part of polycomb repressive complex 2, catalyzes trimethylation of lysine 27 on histone H3 and is involved in proliferation and aggressive cell growth associated with neoplastic cells. EPZ011989 is an orally bioavailable EZH2 inhibitor with Ki values that are less than 3 nM for wild type and Tyr646 mutated EZH2. It displays 15-fold selectivity for EZH2 over EZH1 and is without effect against an array of other lysine methyltransferases. EPZ011989 demonstrates significant tumor growth inhibition in a mouse xenograft model of human B cell lymphoma.
• Uses: N-[(1,2-Dihydro-4,6-dimethyl-2-oxo-3-pyridinyl)methyl]-3-[ethyl[trans-4-[(2-methoxyethyl)methylamino]cyclohexyl]amino]-2-methyl-5-[3-(4-morpholinyl)-1-propyn-1-yl]-benzamide is used in biological studies as inhibitors of EZH2 histone methyltransferase for the treatment of cancer.

Technology Process of EPZ011969

There total 10 articles about EPZ011969 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.3%

3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (771579-27-2) + C27H41N3O4 (1598383-58-4) → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide (1598383-40-4)

Guidance literature:

3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one; C₂₇H₄₁N₃O₄; With triethylamine; In dimethyl sulfoxide; at 20 ℃; for 0.25h;

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dimethyl sulfoxide; at 0 - 20 ℃;

Reference yield:

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-(ethyl)amino)-2-methylbenzoate (1403258-27-4) → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide (1598383-40-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C

1.2: 0 - 20 °C

2.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C

3.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C

4.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere

5.1: sodium hydroxide; water / ethanol / 1 h / 60 °C

6.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C

6.2: 0 - 20 °C

With hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; water; sodium hydride; potassium carbonate; triethylamine; potassium iodide; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (1598383-48-2) → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide (1598383-40-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C

2.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C

3.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere

4.1: sodium hydroxide; water / ethanol / 1 h / 60 °C

5.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C

5.2: 0 - 20 °C

With hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; water; potassium carbonate; triethylamine; potassium iodide; sodium hydroxide; In methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-(ethyl)amino)-2-methylbenzoate

methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate

methyl 5-bromo-3-(ethyl((trans)-4-(methylamino)cyclohexyl)amino)-2-methylbenzoate

3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

Refernces

• 1、 -. "Substituted Benzene Compounds". . . Retrieved 2014/05/07.