carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate

Base Information

• Chemical Name: carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate
• CAS No.: 1350552-40-7
• Molecular Formula: C₂H₄O₂*C₂₉H₃₂F₂N₈O₇
• Molecular Weight: 702.672

Synonyms:carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate

Chemical Property of carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate

Chemical Property:

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Technology Process of carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate

There total 19 articles about carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate 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:

2-Fluoro-3-hydroxy-5-methoxybenzaldehyde (883576-31-6) → carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate (1350552-40-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: guanidine hydrochloride / methanol / 1.5 h / 40 °C / Inert atmosphere

1.2: 22 h / 40 °C

2.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 13.5 h / 70 °C / Inert atmosphere

3.1: water; diammonium sulfide / tetrahydrofuran; methanol / 20 °C

4.1: acetonitrile / 0.83 h / 20 °C / Cooling

5.1: 2,4,6-trimethyl-pyridine / ethyl acetate; toluene / 85 °C

6.1: triethylamine / toluene / 4.17 h / 50 - 110 °C

7.1: acetic acid; 2-picoline borane complex / water; methanol / 24 h / 20 °C

8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 23.5 h / 20 °C

8.2: 0.33 h

9.1: acetyl chloride; methanol / 18.5 h / 5 - 10 °C

9.2: 18 h / 10 - 20 °C

9.3: 18 h / 20 °C

10.1: triethylamine / methanol / 0.25 h / 60 °C

10.2: 23 h / 0 - 20 °C

11.1: hydrogenchloride / ethanol; water; methanol / 20 °C

12.1: potassium carbonate / dimethyl sulfoxide / 96 h / 20 °C

13.1: rubidium carbonate / N,N-dimethyl acetamide / 1 h / 85 °C / Inert atmosphere

14.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 45 °C / Inert atmosphere

With rubidium carbonate; 2,4,6-trimethyl-pyridine; hydrogenchloride; methanol; diammonium sulfide; 2-picoline borane complex; water; guanidine hydrochloride; potassium carbonate; acetic acid; triethylamine; acetyl chloride; sodium iodide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl acetamide; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

1-fluoro-4-methoxybenzene (459-60-9) → carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate (1350552-40-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: n-butyllithium; N,N,N',N'',N'''-pentamethyldiethylenetriamine / hexane; tetrahydrofuran / -70 °C / Inert atmosphere

1.2: 1 h

1.3: -10 - 20 °C

2.1: triethylamine / tetrahydrofuran / 20 °C / Cooling with ice; Inert atmosphere

3.1: n-butyllithium; N,N,N',N'',N'''-pentamethyldiethylenetriamine / hexane; tetrahydrofuran / 3 h / -72 - -56 °C / Inert atmosphere

3.3: 10 - 20 °C

4.1: guanidine hydrochloride / methanol / 1.5 h / 40 °C / Inert atmosphere

4.2: 22 h / 40 °C

5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 13.5 h / 70 °C / Inert atmosphere

6.1: water; diammonium sulfide / tetrahydrofuran; methanol / 20 °C

7.1: acetonitrile / 0.83 h / 20 °C / Cooling

8.1: 2,4,6-trimethyl-pyridine / ethyl acetate; toluene / 85 °C

9.1: triethylamine / toluene / 4.17 h / 50 - 110 °C

10.1: acetic acid; 2-picoline borane complex / water; methanol / 24 h / 20 °C

11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 23.5 h / 20 °C

11.2: 0.33 h

12.1: acetyl chloride; methanol / 18.5 h / 5 - 10 °C

12.2: 18 h / 10 - 20 °C

12.3: 18 h / 20 °C

13.1: triethylamine / methanol / 0.25 h / 60 °C

13.2: 23 h / 0 - 20 °C

14.1: hydrogenchloride / ethanol; water; methanol / 20 °C

15.1: potassium carbonate / dimethyl sulfoxide / 96 h / 20 °C

16.1: rubidium carbonate / N,N-dimethyl acetamide / 1 h / 85 °C / Inert atmosphere

17.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 45 °C / Inert atmosphere

With rubidium carbonate; 2,4,6-trimethyl-pyridine; hydrogenchloride; methanol; diammonium sulfide; n-butyllithium; 2-picoline borane complex; N,N,N',N'',N'''-pentamethyldiethylenetriamine; water; guanidine hydrochloride; potassium carbonate; acetic acid; triethylamine; acetyl chloride; sodium iodide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

tert-butyl(2-fluoro-5-methoxyphenoxy)dimethylsilane (1350551-58-4) → carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetate (1350552-40-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: n-butyllithium; N,N,N',N'',N'''-pentamethyldiethylenetriamine / hexane; tetrahydrofuran / 3 h / -72 - -56 °C / Inert atmosphere

1.3: 10 - 20 °C

2.1: guanidine hydrochloride / methanol / 1.5 h / 40 °C / Inert atmosphere

2.2: 22 h / 40 °C

3.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 13.5 h / 70 °C / Inert atmosphere

4.1: water; diammonium sulfide / tetrahydrofuran; methanol / 20 °C

5.1: acetonitrile / 0.83 h / 20 °C / Cooling

6.1: 2,4,6-trimethyl-pyridine / ethyl acetate; toluene / 85 °C

7.1: triethylamine / toluene / 4.17 h / 50 - 110 °C

8.1: acetic acid; 2-picoline borane complex / water; methanol / 24 h / 20 °C

9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 23.5 h / 20 °C

9.2: 0.33 h

10.1: acetyl chloride; methanol / 18.5 h / 5 - 10 °C

10.2: 18 h / 10 - 20 °C

10.3: 18 h / 20 °C

11.1: triethylamine / methanol / 0.25 h / 60 °C

11.2: 23 h / 0 - 20 °C

12.1: hydrogenchloride / ethanol; water; methanol / 20 °C

13.1: potassium carbonate / dimethyl sulfoxide / 96 h / 20 °C

14.1: rubidium carbonate / N,N-dimethyl acetamide / 1 h / 85 °C / Inert atmosphere

15.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 45 °C / Inert atmosphere

With rubidium carbonate; 2,4,6-trimethyl-pyridine; hydrogenchloride; methanol; diammonium sulfide; n-butyllithium; 2-picoline borane complex; N,N,N',N'',N'''-pentamethyldiethylenetriamine; water; guanidine hydrochloride; potassium carbonate; acetic acid; triethylamine; acetyl chloride; sodium iodide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

1-fluoro-4-methoxybenzene

2-Fluoro-3-hydroxy-5-methoxybenzaldehyde

carbonic acid 2-{3-[(4-cyanophenylamino)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]-2-fluoro-5-methoxyphenoxy}ethyl ester methyl ester

tert-butyl(2-fluoro-5-methoxyphenoxy)dimethylsilane

Downstream raw materials:

carbonic acid 5-{(R)-(4-{amino[2-ethoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester2-fluoro-1,l-dimethylethyl ester

carbonic acid 5-{(R)-(4-{amino[2-propoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester2-fluoro-1,l-dimethylethyl ester

carbonic acid 5-{(R)-(4-{amino[2-butoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester2-fluoro-1,l-dimethylethyl ester

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