(2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

Base Information

• Chemical Name: (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
• CAS No.: 1616340-94-3
• Molecular Formula: C₂₂H₂₀F₃N₃O₅
• Molecular Weight: 463.413
• Mol file: 1616340-94-3.mol

Synonyms:(2R,5S,13aR)-8-methoxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1‘,2’:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

Chemical Property of (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

Chemical Property:

• Boiling Point: 697.6±55.0 °C(Predicted)
• PKA: 10.29±0.20(Predicted)
• Density: 1.53±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(2R,5S,13aR)-8-Methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1'',2'':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

There total 9 articles about (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide 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:

methyl 1-(2,2-dihydroxyethyl)-3-methoxy-4-oxo-5-((2,4,6-trifluorobenzyl) carbamoyl)-1,4-dihydropyridine-2-carboxylate + (1R,3S)-3-aminocyclopentan-1-ol hydrochloride (124555-33-5,1259436-59-3,1523541-74-3,1284248-73-2,1523530-42-8) → (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1‘,2’:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide (1616340-94-3)

Guidance literature:

With potassium acetate; In dichloromethane; at 40 - 50 ℃;

Reference yield:

(2,4,6-trifluorophenyl)methanamine (214759-21-4) + (2R,5S,13aR)-8-methoxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid (1616342-45-0) + pivaloyl chloride (3282-30-2) → (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1‘,2’:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide (1616340-94-3)

Guidance literature:

(2R,5S,13aR)-8-methoxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid; pivaloyl chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 - 30 ℃; for 1h;

(2,4,6-trifluorophenyl)methanamine; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 - 30 ℃; for 2h;

With dmap; succinic acid; for 4h; Reflux;

Reference yield:

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid (1335210-23-5) → (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1‘,2’:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide (1616340-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1: methanesulfonic acid; acetic acid / acetonitrile / 81 h / -10 - 75 °C

2: potassium carbonate / acetonitrile / 2 h / 85 °C

3: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 1.5 h

With methanesulfonic acid; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; In acetonitrile;

upstream raw materials:

1-(2,2-dihydroxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid

(1R,3S)-3-aminocyclopentan-1-ol hydrochloride

(2,4,6-trifluorophenyl)methanamine

Downstream raw materials:

GS-9883

Refernces

• 1、 -. "PROCESS AND POLYMORPHIC FORMS OF BICTEGRAVIR AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS OR CO-CRYSTALS THEREOF". Page/Page column 40. . Retrieved 2021/01/22.
• 2、 -. "POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR PHARMACEUTICAL USE". . . Retrieved 2014/07/08.