2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

Base Information

Chemical Name:2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide
CAS No.:863102-04-9
Molecular Formula:C₂₁H₁₉ClN₂O₃S
Molecular Weight:414.912
Hs Code.:

2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-<i>b</i>]pyridine-5-carboxylic acid 4-chloro-benzylamide

Synonyms:2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

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Chemical Property of 2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

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Technology Process of 2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

There total 5 articles about 2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide 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: 84.0%

: 292143-90-9
N-(4-chlorobenzyl)-2-iodo-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

: 5390-04-5
pent-1-yn-5-ol

: 863102-04-9
2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; at 20 ℃; for 18h;
DOI:10.1021/jm050162b

Reference yield:

: 292143-49-8
N-(4-chlorobenzyl)-4-hydroxythieno[2,3-b]pyridine-5-carboxamide

: 863102-04-9
2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / sodium acetate; iodine monochloride / CHCl₃; methanol / 1 h / 20 °C

2: 92 percent / K₂CO₃ / dimethylformamide / 18 h / 90 °C

3: 84 percent / copper(I) iodide; PdCl₂(PPh₃)2; Et₂NH / 18 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium acetate; Iodine monochloride; potassium carbonate; diethylamine; In methanol; chloroform; N,N-dimethyl-formamide; 3: Sonogashira coupling;
DOI:10.1021/jm050162b

Reference yield:

: 292143-52-3,863101-95-5
N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide

: 863102-04-9
2-(5-hydroxy-pent-1-ynyl)-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid 4-chloro-benzylamide

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃ / dimethylformamide / 18 h / 90 °C

2: 84 percent / copper(I) iodide; PdCl₂(PPh₃)2; Et₂NH / 18 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; diethylamine; In N,N-dimethyl-formamide; 2: Sonogashira coupling;
DOI:10.1021/jm050162b