(+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt

Base Information

• Chemical Name: (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt
• CAS No.: 1422851-31-7
• Molecular Formula: CH₂O₂*C₁₉H₁₉ClFN₅O₂
• Molecular Weight: 449.869

Synonyms:(+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt

Chemical Property of (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt

Chemical Property:

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Technology Process of (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt

There total 12 articles about (+)-N¹-(4-chloro-3-fluorophenyl)-N²-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt 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: 75.0%

formic acid (64-18-6) + N1-((1R,2R)-2-(aminomethyl)-2,3-dihydro-1H-inden-1-yl)-N2-(4-chloro-3-fluorophenyl)-oxalamide (1422851-67-9) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → (+)-N1-(4-chloro-3-fluorophenyl)-N2-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt (1422851-31-7)

Guidance literature:

N¹-((1R,2R)-2-(aminomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl)-oxalamide; 1H-pyrazole-1-carboximidamide hydrochloride; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 65 ℃; for 3h; Inert atmosphere;

formic acid;

DOI:10.1021/ml300407y

Reference yield:

N1-(4-chloro-3-fluorophenyl)-N2-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide (1422851-50-0) → (+)-N1-(4-chloro-3-fluorophenyl)-N2-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt (1422851-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium azide / dimethyl sulfoxide / 3 h / 70 °C / Inert atmosphere

3.1: palladium on activated charcoal; hydrogen / ethyl acetate / 2.5 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 65 °C / Inert atmosphere

4.2: preparative scale HPLC

With sodium azide; palladium on activated charcoal; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ml300407y

Reference yield:

[(1R,2S)-1-{(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2,3-dihydro-1H-inden-2-yl}methyl] methanesulfonate (1422851-70-4) → (+)-N1-(4-chloro-3-fluorophenyl)-N2-(trans-2-(guanidinomethyl)indan-1-yl)oxalamide formate salt (1422851-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium azide / dimethyl sulfoxide / 3 h / 70 °C / Inert atmosphere

2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 2.5 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 65 °C / Inert atmosphere

3.2: preparative scale HPLC

With sodium azide; palladium on activated charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ml300407y

upstream raw materials:

formic acid

N¹-((1R,2R)-2-(aminomethyl)-2,3-dihydro-1H-inden-1-yl)-N²-(4-chloro-3-fluorophenyl)-oxalamide

1H-pyrazole-1-carboximidamide hydrochloride

N¹-(4-chloro-3-fluorophenyl)-N²-((1R,2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)oxalamide

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