6-chloro-9-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine

Base Information

• Chemical Name: 6-chloro-9-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine
• CAS No.: 848695-25-0
• Molecular Formula: C14H15ClN6O
• Molecular Weight: 318.766
• Hs Code.: 2933990090
• European Community (EC) Number: 812-781-2
• UNII: 851B9FQ7Q0
• ChEMBL ID: CHEMBL467399
• DSSTox Substance ID: DTXSID601025952
• Metabolomics Workbench ID: 153359
• NCI Thesaurus Code: C62517
• Nikkaji Number: J3.159.783H
• Pharos Ligand ID: GWFT1SGHCH39
• Wikidata: Q27075249
• Mol file: 848695-25-0.mol

Synonyms:6-chloro-4MDMPA;6-chloro-9-(4-methoxy-3,5-dimethylpyridin-2-ylmethyl)-9H-purin-2-ylamine;BIIB021;CNF 2024;CNF-2024;CNF2024

Chemical Property of 6-chloro-9-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine

Chemical Property:

• Melting Point: 192-193℃
• Boiling Point: 588.5±60.0 °C(Predicted)
• PKA: 6.07±0.40(Predicted)
• PSA: 91.74000
• Density: 1.50
• LogP: 2.71180
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (>25 mg/ml)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 318.0995868
• Heavy Atom Count: 22
• Complexity: 388

Purity/Quality:

98% min ^*data from raw suppliers

BIIB 021 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CN2C=NC3=C2N=C(N=C3Cl)N
• Recent ClinicalTrials: Once or Twice Daily Administration of BIIB021 to Subjects With Advanced Solid Tumors
• Recent EU Clinical Trials: Phase 2a, open-label, randomized, noncomparative study of BIIB021 in combination with exemestane in women with hormone receptor-positive, advanced metatatic breast cancer who have progressed on a nonsteroidal aromatase inhibitor
• Description: BIIB021 is a potent HSP90 inhibitor (IC50 = 30 nM HER-2 degradation).1 It inhibited the proliferation of MCF7 and BT474 breast cancer cell lines (IC50 = 100 nM for each).? BIIB021 has shown efficacy as a therapeutic in multiple cancer models.2-5
• Uses: BIIB 021 an orally available, fully synthetic small-molecule inhibitor of the heat shock protein Hsp90. Studies show that BIIB 021 adminisitration led to degradation of Hsp90 client proteins measured in tumor tissue and resulted in the inhibition of tumor growth in several human tumor xenograft models.

Technology Process of 6-chloro-9-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine

There total 4 articles about 6-chloro-9-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine 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: 77.0%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 2-amino-6-chloropurine (10310-21-1) → BIIB021 (848695-25-0)

Guidance literature:

2-amino-6-chloropurine; With potassium carbonate; In dimethyl sulfoxide; at 48 ℃; for 0.5h;

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride; In dimethyl sulfoxide; at 22 - 48 ℃; for 12.5h;

Reference yield: 77.0%

2-chloromethyl-3,5-dimethylpyridine hydrochloride (73590-93-9) + 2-amino-6-chloropurine (10310-21-1) → BIIB021 (848695-25-0)

Guidance literature:

2-amino-6-chloropurine; With potassium carbonate; In dimethyl sulfoxide; at 48 ℃; for 0.5h;

2-chloromethyl-3,5-dimethylpyridine hydrochloride; In dimethyl sulfoxide; at 22 - 48 ℃; for 13.5h;

Reference yield:

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 2-Amino-6-chloropurin (10310-21-1) → BIIB021 (848695-25-0) + 6-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-purin-2-amine + 6-chloro-N-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-9H-purin-2-amine + C23H26ClN7O2

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 42 - 52 ℃; Reagent/catalyst; Solvent; Temperature; Concentration; Large scale;

DOI:10.1021/op5003903

upstream raw materials:

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride

2-Amino-6-chloropurin

2-amino-6-chloropurine

2-chloromethyl-3,5-dimethylpyridine hydrochloride

Refernces

• 1、 -. "A O-nitroaryloxy acylated derivative compounds, preparation method and application thereof (by machine translation)". Paragraph 0014-0016. . Retrieved 2018/04/21.
• 2、 -. "NOVEL HETEROCYCLIC COMPOUNDS AS HSP90-INHIBITORS". Page/Page column 303. . Retrieved 2008/06/13.