N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Base Information

• Chemical Name: N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
• CAS No.: 1202055-67-1
• Molecular Formula: C₃₈H₄₆N₈O₃
• Molecular Weight: 662.835

Synonyms:N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property of N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property:

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Technology Process of N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

There total 9 articles about N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}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-methoxybenzoic acid (1202055-53-5) + (S)-2-(1-pyrrolidinylmethyl)pyrrolidine (51207-66-0) → N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1202055-67-1)

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:

8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid → N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1202055-67-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

4: 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⁾; 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; XPhos; In 1,4-dioxane; N,N-dimethyl-formamide; 2: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmcl.2011.05.122

Reference yield:

8-amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1202057-03-1) → N-(2,6-diethylphenyl)-8-[(2-methoxy-4-{[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]carbonyl}phenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1202055-67-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 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⁾; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; XPhos; In 1,4-dioxane; N,N-dimethyl-formamide; 1: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmcl.2011.05.122

upstream raw materials:

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-methoxybenzoate

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

(S)-2-(1-pyrrolidinylmethyl)pyrrolidine

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