2-Chloro-3-methyl-4-[(7R,7AS)-tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]benzonitrile

Base Information

• Chemical Name: 2-Chloro-3-methyl-4-[(7R,7AS)-tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]benzonitrile
• CAS No.: 627530-84-1
• Molecular Formula: C14H12ClN3O3
• Molecular Weight: 305.721
• European Community (EC) Number: 806-265-6
• UNII: 9BLW27W4X7
• DSSTox Substance ID: DTXSID50432357
• Wikipedia: BMS-564,929
• Wikidata: Q4836003
• Pharos Ligand ID: TXH8PP5PHVZ9
• Metabolomics Workbench ID: 150467
• ChEMBL ID: CHEMBL229264
• Mol file: 627530-84-1.mol

Synonyms:(7R,7aS)-2-(3-chloro-4-cyano-2-methylphenyl)-7-hydroxytetrahydro-2H-pyrrolo(1,2-e)imidazole-1,3-dione;BMS-564929

Chemical Property of 2-Chloro-3-methyl-4-[(7R,7AS)-tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]benzonitrile

Chemical Property:

• Boiling Point: 523.3±60.0 °C(Predicted)
• PKA: 13.38±0.20(Predicted)
• PSA: 84.64000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: 1.42478
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 305.0567189
• Heavy Atom Count: 21
• Complexity: 531

Purity/Quality:

98%,99%, ^*data from raw suppliers

BMS-564929 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1Cl)C#N)N2C(=O)C3C(CCN3C2=O)O
• Isomeric SMILES: CC1=C(C=CC(=C1Cl)C#N)N2C(=O)[C@@H]3[C@@H](CCN3C2=O)O
• Uses: BMS-564929 is a selective androgen receptor modulator that induces anabolic effects. Potential use in osteoporosis treatments; SARMs

Technology Process of 2-Chloro-3-methyl-4-[(7R,7AS)-tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]benzonitrile

There total 7 articles about 2-Chloro-3-methyl-4-[(7R,7AS)-tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]benzonitrile 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:

(2S,3R)-1-(3-Chloro-4-cyano-2-methylphenylcarbamoyl)-3-hydroxypyrrolidine-2-carboxylic Acid Methyl Ester (627531-49-1) → BMS-564929 (627530-84-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2007.01.076

Reference yield:

N-(3-chloro-2-methylphenyl)acetamide (7463-35-6) → BMS-564929 (627530-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Br₂

2: Pd(dba)2 / dimethylformamide

3: aq. HCl / ethanol

4: NaHCO₃ / CH₂Cl₂

5: i-Pr₂NEt / toluene

6: DBU / toluene / 12 h / 20 °C

With hydrogenchloride; bromine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2007.01.076

Reference yield:

N-(4-bromo-3-chloro-2-methylphenyl)acetamide (125328-80-5) → BMS-564929 (627530-84-1)

Guidance literature:

Multi-step reaction with 5 steps

1: Pd(dba)2 / dimethylformamide

2: aq. HCl / ethanol

3: NaHCO₃ / CH₂Cl₂

4: i-Pr₂NEt / toluene

5: DBU / toluene / 12 h / 20 °C

With hydrogenchloride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2007.01.076

upstream raw materials:

(2S,3R)-1-(3-Chloro-4-cyano-2-methylphenylcarbamoyl)-3-hydroxypyrrolidine-2-carboxylic Acid Methyl Ester

4-amino-2-chloro-3-methyl-benzonitrile

2-chloro-4-isocyanato-3-methyl-benzonitrile

N-(3-chloro-4-cyano-2-methylphenyl)acetamide

Refernces