3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one

Base Information

• Chemical Name: 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one
• CAS No.: 2262452-06-0
• Molecular Formula: C₁₉H₁₂Cl₂N₄O₃
• Molecular Weight: 415.235

Synonyms:

Chemical Property of 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one

Chemical Property:

• Boiling Point: 658.2±65.0 °C(Predicted)
• Density: 1.73±0.1 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

RU-521 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: RU.521 (2262452-06-0) is an inhibitor of cyclic GMP-AMP synthase (cGAS), an important innate immune system sensor of foreign cytoplasmic double-stranded DNA.1,2 IC50 = 0.70 μM in dsDNA-stimulated RAW macrophages1 and ~0.80 μM in wild type human THP-1 cells2. It is selective for cGAS with no targeting of IFNB1 protein, interferon receptors, or downstream signaling components of the JAK/STAT pathway. RU.521 was able to significantly increase cardiac output in a mouse model of sepsis.3 Active in both mouse and human cell lines.

Technology Process of 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one

There total 5 articles about 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-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: 19.27%

(6,7-dichloro-1H-benzimidazol-2-yl)hydrazine + ethyl 3-oxo-2-<3-oxo-1,3-dihydroisobenzofuran-1-yl>butanoate (731773-32-3) → 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one (2262452-06-0)

Guidance literature:

In acetic acid; at 25 - 50 ℃; for 15h; Inert atmosphere;

DOI:10.1038/s41467-017-00833-9

Reference yield:

4-nitro-1,2,3-trichlorobenzene (17700-09-3) → 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one (2262452-06-0)

Guidance literature:

Multi-step reaction with 6 steps

1: ammonia / methanol / 24 h / 120 °C

2: ammonium chloride; zinc / methanol; water / 2 h / 25 °C / Inert atmosphere

3: pyridine / tetrahydrofuran / 12 h / 25 °C

4: trichlorophosphate / 12 h / 110 °C

5: hydrazine hydrate / 12 h / 100 °C

6: acetic acid / 15 h / 25 - 50 °C / Inert atmosphere

With pyridine; ammonia; ammonium chloride; hydrazine hydrate; zinc; trichlorophosphate; In tetrahydrofuran; methanol; water; acetic acid;

DOI:10.1038/s41467-017-00833-9

Reference yield:

2,3-dichloro-6-nitroaniline (65078-77-5) → 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one (2262452-06-0)

Guidance literature:

Multi-step reaction with 5 steps

1: ammonium chloride; zinc / methanol; water / 2 h / 25 °C / Inert atmosphere

2: pyridine / tetrahydrofuran / 12 h / 25 °C

3: trichlorophosphate / 12 h / 110 °C

4: hydrazine hydrate / 12 h / 100 °C

5: acetic acid / 15 h / 25 - 50 °C / Inert atmosphere

With pyridine; ammonium chloride; hydrazine hydrate; zinc; trichlorophosphate; In tetrahydrofuran; methanol; water; acetic acid;

DOI:10.1038/s41467-017-00833-9

upstream raw materials:

ethyl 3-oxo-2-<3-oxo-1,3-dihydroisobenzofuran-1-yl>butanoate

4-nitro-1,2,3-trichlorobenzene

2,3-dichloro-6-nitroaniline

3,4-dichloro-1,2-phenylenediamine

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