4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

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Chemical Name:4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide
CAS No.:1269420-62-3
Molecular Formula:C₂₁H₁₉F₂N₅O₄S
Molecular Weight:475.476
Hs Code.:

Synonyms:4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

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Chemical Property of 4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

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Technology Process of 4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

There total 12 articles about 4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]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: 57.0%

: 1269421-85-3
N-(2,6-difluoro-3-(propylsulfonamido)phenyl)-4-(2,4-dimethoxybenzyl-amino)-6-(3-hydroxyprop-1-ynyl)quinazoline-8-carboxamide

: 1269420-62-3
4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

Guidance literature:: N-(2,6-difluoro-3-(propylsulfonamido)phenyl)-4-(2,4-dimethoxybenzyl-amino)-6-(3-hydroxyprop-1-ynyl)quinazoline-8-carboxamide; With trifluoroacetic acid; at 85 ℃; for 1h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

: 907574-30-5
2-amino-5-iodoisophthalic acid

: 1269420-62-3
4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 0.25 h / 170 - 185 °C

2.1: sulfuric acid / 32 h / Reflux

3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h

3.2: 48 h / 20 °C

4.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

5.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 65 °C

5.2: pH 5 / Acidic conditions

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C

7.1: trifluoroacetic acid / 1 h / 85 °C

With lithium hydroxide monohydrate; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 83141-10-0
2,6-difluoro-3-nitrobenzoic acid

: 1269420-62-3
4-amino-6-(3-hydroxy-prop-1-ynyl)-quinazoline-8-carboxylic acid [2,6-difluoro-3-(propane-1-sulfonyl-amino)phenyl]amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: methanol / 2 h / Cooling with water bath

2.1: hydrogen / palladium 10% on activated carbon / ethanol / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with water bath

4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C

5.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C

5.2: 15 h / 80 °C

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C

7.1: trifluoroacetic acid / 1 h / 85 °C

With methanol; diphenyl phosphoryl azide; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 5.2: Curtius Rearrangement;