5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one

Base Information

• Chemical Name: 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one
• CAS No.: 1346669-85-9
• Molecular Formula: C₃₀H₃₀FN₅O₃S
• Molecular Weight: 559.664

Synonyms:5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one

Chemical Property of 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one

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Technology Process of 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one

There total 15 articles about 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1⁽⁹⁾,2⁽⁷⁾-dien-6-one 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: 70.0%

(2-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxopyridin-3-yl}-4-fluoro-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.0(2,7)]trideca-1(9),2(7)-dien-5-yl}phenyl)methyl acetate (1346673-39-9) → 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1(9),2(7)-dien-6-one (1346669-85-9)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; isopropyl alcohol; at 30 ℃; for 2h;

Reference yield:

4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid (40133-07-1) → 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1(9),2(7)-dien-6-one (1346669-85-9)

Guidance literature:

Multi-step reaction with 11 steps

1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / 0 - 20 °C

3: tetrahydrofuran / 4 h / -10 - 0 °C / Inert atmosphere

4: hydrogenchloride / dichloromethane; diethyl ether / 1 h / 20 °C

5: sulfuric acid / 16 h / 95 °C

6: hydroxylamine hydrochloride; sodium acetate / methanol / 16 h / 20 °C / Inert atmosphere

7: polyphosphoric acid / 16 h / 80 °C / Inert atmosphere

8: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

9: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

10: potassium phosphate; sodium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2 h / 110 °C / sealed vial

11: water; lithium hydroxide / isopropyl alcohol; tetrahydrofuran / 2 h / 30 °C

With hydrogenchloride; potassium phosphate; oxalyl dichloride; sulfuric acid; hydroxylamine hydrochloride; water; potassium acetate; sodium acetate; caesium carbonate; triethylamine; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N,N-dimethyl-formamide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetonitrile;

Reference yield:

4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid chloride (65361-26-4) → 5-(3-{5-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-5-fluoro-2-(hydroxymethyl)phenyl)-8-thia-5-azatricyclo-[7.4.0.0(2,7)]trideca-1(9),2(7)-dien-6-one (1346669-85-9)

Guidance literature:

Multi-step reaction with 10 steps

1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

2: tetrahydrofuran / 4 h / -10 - 0 °C / Inert atmosphere

3: hydrogenchloride / dichloromethane; diethyl ether / 1 h / 20 °C

4: sulfuric acid / 16 h / 95 °C

5: hydroxylamine hydrochloride; sodium acetate / methanol / 16 h / 20 °C / Inert atmosphere

6: polyphosphoric acid / 16 h / 80 °C / Inert atmosphere

7: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

8: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

9: potassium phosphate; sodium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 2 h / 110 °C / sealed vial

10: water; lithium hydroxide / isopropyl alcohol; tetrahydrofuran / 2 h / 30 °C

With hydrogenchloride; potassium phosphate; sulfuric acid; hydroxylamine hydrochloride; water; potassium acetate; sodium acetate; caesium carbonate; triethylamine; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetonitrile;

upstream raw materials:

4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid

4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid chloride

5-cyclopropyl-2H-pyrazol-3-ylamine

5-amino-3-cyclopropyl-1H-pyrazole-1-carboxylic acid tert-butyl ester

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