tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate

Base Information

• Chemical Name: tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate
• CAS No.: 790230-42-1
• Molecular Formula: C₃₁H₃₆N₄O₅
• Molecular Weight: 544.651
• Mol file: 790230-42-1.mol

Synonyms:tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate

Chemical Property of tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate

There total 17 articles about tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate 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:

2'-(3-carboxy-phenylcarbamoyl)-4-isobutylcarbamoyl-4'-methylamino-biphenyl-2-carboxylic acid tert-butyl ester (790230-16-9) → tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate (790230-42-1)

Guidance literature:

With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2006.08.010

Reference yield:

4-bromo-3-(hydroxymethyl)benzoic acid (790230-04-5) → tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate (790230-42-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 4.27 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

2.1: MnO₂ / CHCl₃ / 1 h / 70 °C

3.1: 3.53 g / 4-methylbenzenesulfonic acid monohydrate / toluene / 12 h / Heating

4.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C

4.2: triisopropyl borate / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

4.3: 280 mg / hydrochloric acid / tetrahydrofuran; hexane; H₂O / 3 h / 20 °C

5.1: K₃PO₄ / Pd(PPh₃)4 / dimethylformamide / 24 h / 120 °C

6.1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol; H₂O; acetonitrile / 12 h / 20 °C

7.1: 2.15 g / MgSO₄; H₂SO₄ / CH₂Cl₂

8.1: 1.23 g / NaOH / methanol; H₂O / 2 h / Heating

9.1: 1.28 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 80 °C

10.1: 1.00 g / hydrogen / Pd/C / methanol / 12 h / 20 °C

11.1: pyridine / CH₂Cl₂ / 72 h / 20 °C

12.1: 190 mg / K₂CO₃ / butan-2-one / 4 h / 40 °C

13.1: 115 mg / NaOH / methanol; H₂O / 2 h / Heating

14.1: 78 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole; NH₄Cl / ethyldiisopropylamine / dimethylformamide / 12 h / 20 °C

With pyridine; manganese(IV) oxide; sodium hydroxide; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen; magnesium sulfate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 5.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.08.010

Reference yield:

4-bromo-3-formyl-N-isobutyl-benzamide → tert-butyl 2'-{[3-(aminocarbonyl)phenyl]amino}carbonyl-4-(isobutylamino)carbonyl-4'-(methylamino)biphenyl-2-carboxylate (790230-42-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 3.53 g / 4-methylbenzenesulfonic acid monohydrate / toluene / 12 h / Heating

2.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: triisopropyl borate / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2.3: 280 mg / hydrochloric acid / tetrahydrofuran; hexane; H₂O / 3 h / 20 °C

3.1: K₃PO₄ / Pd(PPh₃)4 / dimethylformamide / 24 h / 120 °C

4.1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol; H₂O; acetonitrile / 12 h / 20 °C

5.1: 2.15 g / MgSO₄; H₂SO₄ / CH₂Cl₂

6.1: 1.23 g / NaOH / methanol; H₂O / 2 h / Heating

7.1: 1.28 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 80 °C

8.1: 1.00 g / hydrogen / Pd/C / methanol / 12 h / 20 °C

9.1: pyridine / CH₂Cl₂ / 72 h / 20 °C

10.1: 190 mg / K₂CO₃ / butan-2-one / 4 h / 40 °C

11.1: 115 mg / NaOH / methanol; H₂O / 2 h / Heating

12.1: 78 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole; NH₄Cl / ethyldiisopropylamine / dimethylformamide / 12 h / 20 °C

With pyridine; sodium hydroxide; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen; magnesium sulfate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 3.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.08.010

upstream raw materials:

2'-(3-carboxy-phenylcarbamoyl)-4-isobutylcarbamoyl-4'-methylamino-biphenyl-2-carboxylic acid tert-butyl ester

4-bromo-3-(hydroxymethyl)benzoic acid

methyl 3-(acetyloxy)methyl-4-bromobenzoate

4-bromo-3-hydroxymethyl-N-isobutylbenzamide