3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacidhydrochloride

Base Information

• Chemical Name: 3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacidhydrochloride
• CAS No.: 1160221-26-0
• Molecular Formula: C24H19ClF2N2O5
• Molecular Weight: 488.875
• Mol file: 1160221-26-0.mol

Synonyms:3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid hydrochloride;3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)butylbenzoic acid hydrochloride;3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoic acid hydrochloride;Lumacaftor hydrochloride;

Chemical Property of 3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacidhydrochloride

Chemical Property:

• PSA: 97.75000
• LogP: 5.62200

Purity/Quality:

98%min ^*data from raw suppliers

3-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid hydrochloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacidhydrochloride

There total 20 articles about 3-(6-{[1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacidhydrochloride 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:

tert-butyl 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoate (1160221-25-9) → Lumacaftor hydrochloride (1160221-26-0)

Guidance literature:

With hydrogenchloride; water; In acetonitrile; at 45 ℃; for 24 - 48h;

Reference yield:

3-Carboxyphenylboronic acid (25487-66-5) + N-(6-bromo-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide → Lumacaftor hydrochloride (1160221-26-0)

Guidance literature:

N-(6-bromo-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; ethanol; water; at 20 ℃; for 1h;

3-Carboxyphenylboronic acid; In 1,4-dioxane; ethanol; water; at 85 - 90 ℃; for 4h;

With hydrogenchloride; In water; acetone; at 20 ℃; for 12h;

Reference yield:

2-bromo-3-picoline (3430-17-9) → Lumacaftor hydrochloride (1160221-26-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / toluene; water / 1 h / 65 °C / Inert atmosphere

1.2: 2 h / 80 °C / Inert atmosphere

2.1: urea hydrogen peroxide adduct; phthalic anhydride / water; ethyl acetate / 45 °C

3.1: Methanesulfonic anhydride; pyridine / acetonitrile / 1.33 h / 70 - 75 °C

3.2: 2 h / 20 °C

4.1: triethylamine; dmap / toluene / 2 h

5.1: hydrogenchloride; water / acetonitrile / 40 - 45 °C

With pyridine; hydrogenchloride; dmap; phthalic anhydride; water; urea hydrogen peroxide adduct; potassium carbonate; triethylamine; Methanesulfonic anhydride; In water; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

tert-butyl 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoate

2-bromo-3-picoline

tert-butyl 3-(3-methylpyridin-2-yl)benzoate

tert-butyl 3-(3-methyl-1-oxo-1λ-pyridin-2-yl)benzoate

Downstream raw materials:

Lumacaftor

Refernces

• 1、 -. "PHARMACEUTICAL COMPOSITIONS OF 3-(6-(1-(2,2-DIFLUOROBENZO[D][1,3]DIOXOL-5-YL)CYCLOPROPANECARBOXAMIDO)-3-METHYLPYRIDIN-2-YL)BENZOIC ACID AND ADMINISTRATION THEREOF". Sheet 79; 80. . Retrieved 2019/03/09.
• 2、 -. "FORMULATIONS OF 3-(6-(1-(2,2-DIFLUOROBENZO[D][1,3]DIOXOL-5-YL) CYCLOPROPANECARBOXAMIDO)-3-METHYLPYRIDIN-2-YL)BENZOIC ACID". Paragraph 0375; 0376. . Retrieved 2016/11/28.