4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid

Base Information

• Chemical Name: 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid
• CAS No.: 1165798-05-9
• Molecular Formula: C₃₀H₃₅N₃O₅
• Molecular Weight: 517.625

Synonyms:4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid

Chemical Property of 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid

Chemical Property:

Purity/Quality:

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Technology Process of 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid

There total 4 articles about 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid 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: 39.0%

4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid methyl ester (1165799-98-3) → 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid (1165798-05-9)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

2-chloroquinoline-4-carboxylic acid (5467-57-2) → 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid (1165798-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

2.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; 1.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

4-methoxycarbonylphenylboronic acid (99768-12-4) → 4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid (1165798-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

2.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; 1.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

upstream raw materials:

4-(4-{[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzoic acid methyl ester

2-[4-(methoxycarbonyl)phenyl]quinoline-4-carboxylic acid

trans-((4-aminomethyl)cyclohexylmethyl)carbamic acid tert-butyl ester

2-chloroquinoline-4-carboxylic acid

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