Bictegravir

Base Information

• Chemical Name: Bictegravir
• CAS No.: 1611493-60-7
• Molecular Formula: C21H18F3N3O5
• Molecular Weight: 449.386
• Mol file: 1611493-60-7.mol

Synonyms:Bictegravir;GS-9883

Chemical Property of Bictegravir

Chemical Property:

• Boiling Point: 682.5±55.0 °C(Predicted)
• PKA: 4.50±1.00(Predicted)
• PSA: 100.87000
• Density: 1.62±0.1 g/cm3(Predicted)
• LogP: 1.96320
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%Min. ^*data from raw suppliers

Bictegravir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Bictegravir (BIC) is a second-generation integrase strand transfer inhibitor (InSTI), like dolutegravir, with higher genetic barrier to resistance than raltegravir and elvitegravir. Bictegravir is a human immunodeficiency virus (HIV) integrase strand transfer inhibitor, the fourth in this class of agents that target the viral integrase. Bictegravir is used only in combination with other antiretroviral agents in the treatment of HIV infection and it has had limited use. Bictegravir is associated with a low rate of serum aminotransferase elevations during therapy, but has not been linked to instances of acute, clinically apparent liver injury.
• Uses: Bictegravir, is a novel, potent inhibitor of HIV-1 integrase with an IC50 of 7.5 nM.

Technology Process of Bictegravir

There total 13 articles about Bictegravir 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: 85.0%

(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) → GS-9883 (1611493-60-7)

Guidance literature:

With lithium bromide; In tetrahydrofuran; at 60 ℃; Flow reactor;

Reference yield: 78.0%

lithium (2R,5S,13aR)-7,9-dioxo-10-((2,4,6-trifluorobenzyl)carbamoyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepin-8-olate → GS-9883 (1611493-60-7)

Guidance literature:

With hydrogenchloride; In methanol; water; at 20 - 30 ℃; for 1h; pH=2 - 3;

Reference yield:

(2,4,6-trifluorophenyl)methanamine (214759-21-4) + C14H14N2O6 → GS-9883 (1611493-60-7)

Guidance literature:

C₁₄H₁₄N₂O₆; With 1,1'-carbonyldiimidazole; at 40 - 50 ℃; for 5h;

(2,4,6-trifluorophenyl)methanamine; for 1h; Reagent/catalyst; Temperature;

upstream raw materials:

(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

(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

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

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF SODIUM (2R,5S,13AR)-7,9-DIOXO-10-((2,4,6-TRIFLUOROBENZYL)CARBAMOYL)-2,3,4,5,7,9,13,13A-OCTAHYDRO-2,5-METHANOPYRIDO[1', 2':4,5]PYRAZINO[2,1-B] [1,3] OXAZEPIN-8-OLATE AND ITS POLYMORPHIC FORM". . . Retrieved 2020/01/24.
• 2、 -. "CONTINUES FLOW PROCESS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS - POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES AND INTERMEDIATES THEREOF". . . Retrieved 2019/09/04.