di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate

Base Information

• Chemical Name: di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate
• CAS No.: 1351438-86-2
• Molecular Formula: C₂₅H₄₂N₄O₄
• Molecular Weight: 462.633

Synonyms:di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate

Chemical Property of di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate

Chemical Property:

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Technology Process of di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate

There total 7 articles about di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate 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: 86.0%

5,5-[3-(dimethylamino)propyl]-2-isopropylaniline (1350816-47-5) + N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) → di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate (1351438-86-2)

Guidance literature:

With mercury (II) chloride; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm2011172

Reference yield:

(2E)-3-(4-bromo-3-nitrophenyl)-N,N-dimethylacrylamide (1350816-43-1) → di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate (1351438-86-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 15 h / 80 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate

3.1: borane-THF / tetrahydrofuran / 2.5 h / Inert atmosphere; Reflux

3.2: 75 °C

4.1: mercury (II) chloride; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; palladium 10% on activated carbon; hydrogen; sodium carbonate; mercury (II) chloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm2011172

Reference yield:

methyl (2E)-3-(4-bromo-3-nitrophenyl)acrylate → di-tert-butyl [(Z)-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)methylylidene] biscarbamate (1351438-86-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / methanol; water / 5 h / 60 °C

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C

2.2: 2 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 15 h / 80 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate

5.1: borane-THF / tetrahydrofuran / 2.5 h / Inert atmosphere; Reflux

5.2: 75 °C

6.1: mercury (II) chloride; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; palladium 10% on activated carbon; hydrogen; sodium carbonate; potassium carbonate; mercury (II) chloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm2011172

upstream raw materials:

(2E)-3-(4-bromo-3-nitrophenyl)-N,N-dimethylacrylamide

(2E)-3-(4-isopropenyl-3-nitrophenyl)-N,N-dimethylacrylamide

3-(3-amino-4-isopropylphenyl)-N,N-dimethylpropanamide

5,5-[3-(dimethylamino)propyl]-2-isopropylaniline

Downstream raw materials:

9-chloro-2-(5-(3-(dimethylamino)propyl)-2-isopropylphenylamino)-5H-benzo[b]pyrimido[4,5-d]azepin-6(7H)-one

9-chloro-2-({5-[3-(dimethylamino)propyl]-2-isopropylphenyl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepine-6-thione

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