(2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride

Base Information

• Chemical Name: (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride
• CAS No.: 2113650-04-5
• Molecular Formula: C₃₅H₃₄N₂O₇*ClH
• Molecular Weight: 631.125
• Mol file: 2113650-04-5.mol

Synonyms:

Chemical Property of (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride

Chemical Property:

Purity/Quality:

99%+, ^*data from raw suppliers

BMS-1001hydrochloride >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: BMS-1001 is a small molecule inhibitor of the interaction between programmed death protein 1 (PD-1) and its ligand programmed cell death ligand 1 (PD-L1) with an IC50 value of 2.25 nM in a homogeneous time-resolved fluorescence (HTRF) binding assay.

Technology Process of (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride

There total 5 articles about (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid 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:

2.3-dihydro-1,4-benzodioxin-6-ylboronic acid (164014-95-3) → (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride (2113650-04-5)

Guidance literature:

Multi-step reaction with 4 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate / ethanol; toluene / 0.5 h / 80 °C / Inert atmosphere

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 h / 20 °C / Cooling with ice

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C

4: sodium cyanoborohydride; acetic acid / N,N-dimethyl-formamide / 3 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; di-isopropyl azodicarboxylate; sodium cyanoborohydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; 1: |Suzuki-Miyaura Coupling / 2: |Mitsunobu Displacement;

DOI:10.1021/acs.jmedchem.7b00293

Reference yield:

3-bromo-2-methylbenzyl alcohol (83647-43-2) → (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride (2113650-04-5)

Guidance literature:

Multi-step reaction with 4 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate / ethanol; toluene / 0.5 h / 80 °C / Inert atmosphere

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 h / 20 °C / Cooling with ice

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C

4: sodium cyanoborohydride; acetic acid / N,N-dimethyl-formamide / 3 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; di-isopropyl azodicarboxylate; sodium cyanoborohydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; 1: |Suzuki-Miyaura Coupling / 2: |Mitsunobu Displacement;

DOI:10.1021/acs.jmedchem.7b00293

Reference yield:

4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-2-hydroxy-5-methylbenzaldehyde → (2R)-2-[({2-[(3-cyanophenyl)methoxy]-4-{[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy}-5-methylphenyl}methyl)amino]-3-hydroxypropanoic acid hydrochloride (2113650-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

2: sodium cyanoborohydride; acetic acid / N,N-dimethyl-formamide / 3 h / 80 °C

With sodium cyanoborohydride; caesium carbonate; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b00293

upstream raw materials:

3-bromo-2-methylbenzyl alcohol

2.3-dihydro-1,4-benzodioxin-6-ylboronic acid

3-bromo-2-methylbenzoic acid

Refernces