N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Base Information

• Chemical Name: N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
• CAS No.: 1323157-80-7
• Molecular Formula: C₃₃H₃₇F₃N₈O₃
• Molecular Weight: 650.704

Synonyms:N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property of N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

There total 8 articles about N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide 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:

4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)-3-(trifluoromethoxy)benzoic acid (1323157-94-3) + N,N-dimethylethylenediamine (108-00-9) → N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1323157-80-7)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2011.05.122

Reference yield:

ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (802534-49-2) → N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1323157-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: water; potassium hydroxide / ethanol / 1 h / Reflux

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos / 1,4-dioxane / 8 h / 90 °C / Inert atmosphere

4: trifluoroacetic acid / N,N-dimethyl-formamide / 20 °C

5: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; water; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium hydroxide; XPhos; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide; 3: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmcl.2011.05.122

Reference yield:

4-amino-3-(trifluoromethoxy)benzoic acid (175278-22-5) → N-(2,6-diethylphenyl)-8-{[4-{[2-(dimethylamino)ethyl]carbamoyl}-2-(trifluoromethoxy)phenyl]amino}-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1323157-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride; water; sodium nitrite / 0.33 h / 0 °C

1.2: 3 h / 0 °C

2.1: dmap; di-tert-butyl dicarbonate / dichloromethane / 24 h / Reflux

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos / 1,4-dioxane / 8 h / 90 °C / Inert atmosphere

4.1: trifluoroacetic acid / N,N-dimethyl-formamide / 20 °C

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With hydrogenchloride; dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; di-tert-butyl dicarbonate; water; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium nitrite; XPhos; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 3.1: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmcl.2011.05.122

upstream raw materials:

4-amino-3-(trifluoromethoxy)benzoic acid

ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

8-amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

tert-butyl 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazolin-8-yl}amino)-3-(trifluoromethoxy)benzoate

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