N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride

Base Information

• Chemical Name: N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride
• CAS No.: 1386398-54-4
• Molecular Formula: C₂₅H₃₁N₉O*ClH
• Molecular Weight: 510.042

Synonyms:N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride

Chemical Property of N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride

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Technology Process of N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride

There total 10 articles about N₁-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride 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:

(3-{6-[6-(2-morpholin-4-yl-ethylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester (1386399-48-9) → N1-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride (1386398-54-4)

Guidance literature:

(3-{6-[6-(2-morpholin-4-yl-ethylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; for 15h; Reflux;

With sodium hydrogencarbonate; In water;

With hydrogenchloride; In water;

Reference yield:

3-amino-1-phenylpropan-1-ol (5053-63-4) → N1-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride (1386398-54-4)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

2: triphenylphosphine; diethylazodicarboxylate / 2 h / 0 - 20 °C

3: hydrazine hydrate / tetrahydrofuran; methanol; water / 6 h / 65 °C

4: potassium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; DavePhos / 1,4-dioxane / 7.5 h / 132 °C / Inert atmosphere; Sealed tube

5: trifluoroacetic acid / dichloromethane / 15 h / Reflux

With potassium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; DavePhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

Reference yield:

(+/-)-N-(tert-butoxycarbonyl)-3-amino-1-phenylpropan-1-ol (257892-43-6) → N1-{6-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-yl}-1-phenyl-propane-1,3-diamine hydrochloride (1386398-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1: triphenylphosphine; diethylazodicarboxylate / 2 h / 0 - 20 °C

2: hydrazine hydrate / tetrahydrofuran; methanol; water / 6 h / 65 °C

3: potassium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; DavePhos / 1,4-dioxane / 7.5 h / 132 °C / Inert atmosphere; Sealed tube

4: trifluoroacetic acid / dichloromethane / 15 h / Reflux

With potassium carbonate; hydrazine hydrate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; DavePhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

upstream raw materials:

6-bromo-2-pyridinecarbaldehyde

Benzoylacetonitrile

(+/-)-N-(tert-butoxycarbonyl)-3-amino-1-phenylpropan-1-ol

(±)-tert-butyl N-(3-amino-3-phenyl-propyl)carbamate

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