NMS-P118

Base Information

• Chemical Name: NMS-P118
• CAS No.: 1262417-51-5
• Molecular Formula: C20H24F3N3O2
• Molecular Weight: 395.42
• Mol file: 1262417-51-5.mol

Synonyms:NMS-P118;2-[1-(4,4-Difluorocyclohexyl)-4-piperidinyl]-6-fluoro-2,3-dihydro-3-oxo-1H-isoindole-4-carboxamide

Chemical Property of NMS-P118

Chemical Property:

• PSA: 66.64000
• LogP: 3.49880

Purity/Quality:

97% ^*data from raw suppliers

2-[1-(4,4-Difluorocyclohexyl)-4-piperidinyl]-6-fluoro-2,3-dihydro-3-oxo-1H-isoindole-4-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-[1-(4,4-Difluorocyclohexyl)-4-piperidinyl]-6-fluoro-2,3-dihydro-3-oxo-1H-isoindole-4-carboxamide is a nuclear protein poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor. PARP-1 is involved with the signaling and repair of DNA and a target in oncology.

Technology Process of NMS-P118

There total 6 articles about NMS-P118 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: 67.0%

2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carbonitrile (1262418-04-1) → 2-[1-(4,4-difluorocyclohexyl)-piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (1262417-51-5)

Guidance literature:

With sulfuric acid; acetic acid; at 80 ℃; Product distribution / selectivity;

Reference yield:

4-fluoro-2-methylbenzoic acid (321-21-1) → 2-[1-(4,4-difluorocyclohexyl)-piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (1262417-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: [bis(acetoxy)iodo]benzene; iodine; palladium diacetate / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C

2.2: 2 h / 20 °C

3.1: Methyl pivalate; N-Bromosuccinimide; dibenzoyl peroxide / 3 h / 85 °C / Inert atmosphere

4.1: triethylamine / acetonitrile / 4 h / 90 °C / Inert atmosphere

5.1: N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere

6.1: indium(III) chloride; Acetaldehyde oxime / toluene / 1 h / Reflux

With indium(III) chloride; N-Bromosuccinimide; Acetaldehyde oxime; Methyl pivalate; [bis(acetoxy)iodo]benzene; iodine; palladium diacetate; potassium carbonate; triethylamine; dibenzoyl peroxide; In N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: |Rosenmund-van Braun Cyanation;

DOI:10.1021/acs.jmedchem.5b00680

Reference yield:

4-fluoro-2-iodo-6-methyl-benzoic acid methyl ester (877151-07-0) → 2-[1-(4,4-difluorocyclohexyl)-piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (1262417-51-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Methyl pivalate; N-Bromosuccinimide; dibenzoyl peroxide / 3 h / 85 °C / Inert atmosphere

2: triethylamine / acetonitrile / 4 h / 90 °C / Inert atmosphere

3: N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere

4: indium(III) chloride; Acetaldehyde oxime / toluene / 1 h / Reflux

With indium(III) chloride; N-Bromosuccinimide; Acetaldehyde oxime; Methyl pivalate; triethylamine; dibenzoyl peroxide; In N,N-dimethyl-formamide; toluene; acetonitrile; 3: |Rosenmund-van Braun Cyanation;

DOI:10.1021/acs.jmedchem.5b00680

upstream raw materials:

2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carbonitrile

4-fluoro-2-methylbenzoic acid

4-fluoro-2-iodo-6-methyl-benzoic acid

4-fluoro-2-iodo-6-methyl-benzoic acid methyl ester