N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride

Base Information

• Chemical Name: N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride
• CAS No.: 1269408-70-9
• Molecular Formula: C₂₄H₂₄N₄O₂S*ClH
• Molecular Weight: 469.007

Synonyms:N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride

Chemical Property of N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride

Chemical Property:

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Technology Process of N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride

There total 8 articles about N₁-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide 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: 82.0%

1,1-dimethylethyl [(1S)-2-({(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}amino)-2-oxo-1-(2-thienylmethyl)ethyl]carbamate (1269407-64-8) → N1-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride (1269408-70-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h;

Reference yield:

phenol (108-95-2,27073-41-2) → N1-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride (1269408-70-9)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydride / tetrahydrofuran / 0.83 h / 20 °C

2: hydrogen / 20 wt% Pd(OH)2/C / methanol / 3.5 h / 20 °C

3: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 0.17 h / 0 - 20 °C

4: caesium carbonate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 19.5 h / 100 °C / Inert atmosphere

5: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

6: triethylamine; HATU / dichloromethane / 2.25 h / 20 °C

7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

With hydrogenchloride; tert.-butylnitrite; hydrogen; sodium hydride; caesium carbonate; triethylamine; HATU; copper(ll) bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 20 wt% Pd(OH)2/C; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; acetonitrile;

Reference yield:

5-fluoro-2-nitrobenzonitrile (50594-78-0) → N1-{(3S)-1-[2-cyano-4-(phenyloxy)phenyl]-3-pyrrolidinyl}-3-(2-thienyl)-L-alaninamide hydrochloride (1269408-70-9)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydride / tetrahydrofuran / 0.83 h / 20 °C

2: hydrogen / 20 wt% Pd(OH)2/C / methanol / 3.5 h / 20 °C

3: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 0.17 h / 0 - 20 °C

4: caesium carbonate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 19.5 h / 100 °C / Inert atmosphere

5: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

6: triethylamine; HATU / dichloromethane / 2.25 h / 20 °C

7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

With hydrogenchloride; tert.-butylnitrite; hydrogen; sodium hydride; caesium carbonate; triethylamine; HATU; copper(ll) bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 20 wt% Pd(OH)2/C; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; acetonitrile;

upstream raw materials:

phenol

5-fluoro-2-nitrobenzonitrile

2-nitro-5-phenoxybenzonitrile

2-amino-5-phenoxybenzonitrile

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