4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine

Base Information

• Chemical Name: 4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine
• CAS No.: 186549-27-9
• Molecular Formula: C₂₂H₂₄N₄O₄S₂
• Molecular Weight: 472.589
• Mol file: 186549-27-9.mol

Synonyms:

Chemical Property of 4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine

There total 13 articles about 4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine 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:

3-thiophene carboxaldehyde (498-62-4) → RPR120844 (186549-27-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 20 g / aq. H₂SO₄; I₂; HIO₃ / CCl₄; acetic acid / 6 h / Heating

2.1: 42 g / NaBH₄ / tetrahydrofuran / 1 h

3.1: 10 g / Pd(PPh₃)4 / dimethylformamide / 6 h / 80 °C

4.1: 14 g / CBr₄; PPh₃ / tetrahydrofuran / 3 h

5.1: NaH / tetrahydrofuran; dimethylformamide / 3.5 h / 0 - 20 °C

6.1: HCl / ethyl acetate / 4 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 2 h

8.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

8.2: tetrahydrofuran / 2 h / 20 °C

9.1: HCl / ethanol / 6 h / 20 °C

10.1: NH₃ / 24 h

With hydrogenchloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; sulfuric acid; ammonia; iodine; iodic acid; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; 1.1: Iodination / 2.1: Reduction / 3.1: Substitution / 4.1: Bromination / 5.1: Alkylation / 6.1: acidolysis / 7.1: Condensation / 8.1: Metallation / 8.2: Methylation / 9.1: Addition / 10.1: amidation;

DOI:10.1021/jm990040h

Reference yield:

7-hydroxynaphthalene-2-sulfonic acid sodium salt (135-55-7) → RPR120844 (186549-27-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. NaOH / ethanol / 16 h / 20 °C

2.1: 3.80 g / POCl₃; PCl₅ / 4 h / 120 °C

3.1: Et₃N / CH₂Cl₂ / 2 h

4.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

4.2: tetrahydrofuran / 2 h / 20 °C

5.1: HCl / ethanol / 6 h / 20 °C

6.1: NH₃ / 24 h

With hydrogenchloride; sodium hydroxide; phosphorus pentachloride; ammonia; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Methylation / 2.1: Chlorination / 3.1: Condensation / 4.1: Metallation / 4.2: Methylation / 5.1: Addition / 6.1: amidation;

DOI:10.1021/jm990040h

Reference yield:

7-Methoxy-2-naphthalenesulfonyl chloride (56875-60-6) → RPR120844 (186549-27-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Et₃N / CH₂Cl₂ / 2 h

2.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

2.2: tetrahydrofuran / 2 h / 20 °C

3.1: HCl / ethanol / 6 h / 20 °C

4.1: NH₃ / 24 h

With hydrogenchloride; ammonia; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Condensation / 2.1: Metallation / 2.2: Methylation / 3.1: Addition / 4.1: amidation;

DOI:10.1021/jm990040h

upstream raw materials:

3-thiophene carboxaldehyde

7-hydroxynaphthalene-2-sulfonic acid sodium salt

7-Methoxy-2-naphthalenesulfonyl chloride

5-iodo-thiophene-3-carboxaldehyde

Refernces