5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

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Chemical Name:5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide
CAS No.:205055-45-4
Molecular Formula:C₂₁H₁₈N₄O₄S₂
Molecular Weight:454.53
Hs Code.:

Synonyms:5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

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Chemical Property of 5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

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Technology Process of 5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

There total 11 articles about 5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide 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: 61.0%

: 205055-42-1
5-(pyridin-3-yl)thiophene-2-sulfonyl chloride

: 3-(S)-[(3-amino-2-oxopyrrolidin-1-yl)methyl]-4-hydroxybenzonitrile hydrochloride

: 205055-45-4
5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1021/jm990041+

Reference yield:

: 626-55-1,163928-56-1
3-Bromopyridine

: 205055-45-4
5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: Mg / diethyl ether / Heating

1.2: NiCl₂(dppp) / diethyl ether / 20 °C

2.1: n-BuLi / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.2: SO₂(g) / diethyl ether / -78 - 20 °C

3.1: SO₂Cl₂ / hexane; CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: 61 percent / pyridine / 20 °C

With pyridine; n-butyllithium; sulfuryl dichloride; magnesium; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Grignard reaction / 1.2: Arylation / 2.1: Metallation / 2.2: Sulfination / 3.1: Chlorination / 4.1: Sulfonylation;
DOI:10.1021/jm990041+

Reference yield:

: 1761-62-2
5-iodosalicyclaldehyde

: 205055-45-4
5-pyridin-3-ylthiophene-2-sulfonic acid {1-[5-cyano-2-hydroxybenzyl]-2-oxopyrrolidin-3-(S)-yl}amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.08 h / 0 °C

1.2: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 0.75 h / 0 - 20 °C

2.1: NaBH₄ / tetrahydrofuran / 0.17 h / -15 °C

3.1: 69 percent / N-bromosuccinimide; Ph₃P / tetrahydrofuran / 0.5 h / 5 - 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0.08 h / 0 °C

4.2: tetrahydrofuran / 4 h / 0 °C

5.1: 92 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 80 °C

6.1: 88 percent / HCl / ethyl acetate / 0.5 h

7.1: 61 percent / pyridine / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triphenylphosphine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: Bromination / 4.1: Metallation / 4.2: Substitution / 5.1: Substitution / 6.1: Acidolysis / 7.1: Sulfonylation;
DOI:10.1021/jm990041+