(5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide

Base Information

• Chemical Name: (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide
• CAS No.: 1008114-99-5
• Molecular Formula: C₂₄H₂₀N₄O₂S
• Molecular Weight: 428.514
• Mol file: 1008114-99-5.mol

Synonyms:(5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide

Chemical Property of (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide

There total 9 articles about (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide 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: 70.0%

(5S)-2-chloro-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide (1008118-99-7) + phenylboronic acid (98-80-6) → (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide (1008114-99-5)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; N,N-dimethyl-formamide; at 100 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jm200879j

Reference yield:

(S)-2-(2-chloro-5H-chromeno [2,3-b]pyridine-5-yl)-2-methylpropanoic acid → (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide (1008114-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; HATU / acetonitrile / 20 - 80 °C / Inert atmosphere

2: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; HATU; In water; N,N-dimethyl-formamide; acetonitrile; 2: Suzuki coupling;

DOI:10.1021/jm200879j

Reference yield:

α,α-dimethyl-5H-[1]benzopyrano[2,3-b]pyridin-5-acetic acid methyl ester (1008118-79-3) → (5S)-2-phenyl-α,α-dimethyl-N-(1,3,4-thiadiazol-2-yl)-5H-[1]benzopyrano[2,3-b]pyridin-5-acetamide (1008114-99-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: trichlorophosphate / 0.5 h / 90 °C / Inert atmosphere; Neat (no solvent)

3: potassium hydroxide / tetrahydrofuran; methanol; water / 10 h / 65 °C / Inert atmosphere

4: ChiralGel OJ column / methanol / Resolution of racemate; Supercritical fluide chromatography

5: triethylamine; HATU / acetonitrile / 20 - 80 °C / Inert atmosphere

6: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; 3-chloro-benzenecarboperoxoic acid; HATU; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 6: Suzuki coupling;

DOI:10.1021/jm200879j

upstream raw materials:

5H-<1>benzopyrano<2,3-b>pyridin-5-ol

α,α-dimethyl-5H-[1]benzopyrano[2,3-b]pyridin-5-acetic acid methyl ester 1-oxide

2-chloro-α,α-dimethyl-5H-[1]benzopyrano[2,3-b]pyridin-5-acetic acid methyl ester

2-(2-chloro-5H-chromeno[2,3-b]-pyridin-5-yl)-2-methylpropanoic acid