(4-Amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

Base Information

• Chemical Name: (4-Amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone
• CAS No.: 741713-40-6
• Molecular Formula: C18H21 F2 N5 O4 S
• Molecular Weight: 441.459
• UNII: T61871RKRI
• DSSTox Substance ID: DTXSID30225143
• Wikidata: Q27088507
• NCI Thesaurus Code: C64544
• Pharos Ligand ID: ZZ7KN7848XXD
• Metabolomics Workbench ID: 151243
• ChEMBL ID: CHEMBL384304
• Mol file: 741713-40-6.mol

Synonyms:741713-40-6;R547;R-547;(4-amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone;R 547;RO-4584820;Ro 4584820;[4-Amino-2-[(1-methylsulfonylpiperidin-4-yl)amino]pyrimidin-5-yl](2,3-difluoro-6-methoxyphenyl)methanone;[4-amino-2-[(1-methylsulfonylpiperidin-4-yl)amino]pyrimidin-5-yl]-(2,3-difluoro-6-methoxyphenyl)methanone;UNII-T61871RKRI;T61871RKRI;741713-40-6 (free base);RG-547;RO4584820;(4-Amino-2-((1-methylsulfonylpiperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone;5-[(2,3-difluoro-6-Methoxyphenyl)carbonyl]-2-N-(1-Methanesulfonylpiperidin-4-yl)pyriMidine-2,4-diaMine;LIA;(4-Amino-2-{[1-(Methylsulfonyl)piperidin-4-Yl]amino}pyrimidin-5-Yl)(2,3-Difluoro-6-Methoxyphenyl)methanone;4-Amino-2-[(1-methylsulfonylpiperidin-4-yl)amino]pyrimidin-5-yl](2,3-difluoro-6-methoxyphenyl)methanone;2fvd;(4-amino-2-([1-(methylsulfonyl)piperidin-4-yl]amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone;(4-Amino-2-[(1-methylsulfonylpiperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone;D04FHB;MLS006010282;CHEMBL384304;GTPL5707;SCHEMBL2397067;BDBM12621;DTXSID30225143;EX-A105;JRNJNYBQQYBCLE-UHFFFAOYSA-N;HMS3656L13;2,4-Diamino-5-ketopyrimidine 39;BCP02856;MFCD09970629;NSC773094;NSC800859;s2688;AKOS025149095;CCG-269137;CS-0022;DB08094;NSC-773094;NSC-800859;SB19228;CID 6918852;RO 4584820 [WHO-DD];NCGC00346632-01;NCGC00346632-06;AC-36792;HY-10014;MS-27934;SMR004701352;R547, >=98% (HPLC);LS-193675;FT-0687511;SW220191-1;[4-Amino-2-[amino]pyrimidin-5-yl] methanone;J-502762;Q27088507;(4-amino-2-(1-(methylsulfonyl)piperidin-4-ylamino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone;[4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone;[4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6-methoxyphenyl)methanone;[4-Amino-2-[[1-(methylsulfonyl)-4-piperidinyl]amino]-5-pyrimidinyl](2,3-difluoro-6-methoxyphenyl)methanone;4-Amino-2-(1-methylsulfonylpiperidin-4-yl)aminopyrimidin-5-yl(2,3-difluoro-6-methoxyphenyl)methanone

Chemical Property of (4-Amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

Chemical Property:

• Vapor Pressure: 1.19E-19mmHg at 25°C
• Boiling Point: 703.7°C at 760 mmHg
• PKA: 4.22±0.10(Predicted)
• Flash Point: 379.4°C
• PSA: 135.89000
• Density: 1.49
• LogP: 3.08540
• Solubility.: Soluble in DMSO
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 441.12823167
• Heavy Atom Count: 30
• Complexity: 701

Purity/Quality:

99% ^*data from raw suppliers

R547 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)F)F)C(=O)C2=CN=C(N=C2N)NC3CCN(CC3)S(=O)(=O)C
• Recent ClinicalTrials: Postoperative Pain Relief Following Total Hip Arthroplasty. A Comparison Between Intrathecal Morphine (IM) and Local Infiltration Analgesia (LIA)
• Description: R547 is a potent ATP-competitive inhibitor of CDK1/2/4 with Ki of 2 nM/3 nM/1 nM. It is less potent to CDK7 and GSK3α/β, while inactive to other kinases. Phase 1. Cyclin-dependent kinases (Cdks) are critical positive regulators of cell cycle progression and cellular transcription whose dysregulation can lead to the development of cancer. R547 is a diaminopyrimidine compound that inhibits Cdk1/cyclin B, Cdk2/cyclin E, and Cdk4/cyclin D1 (Kis = 1-3 nM). It is inactive against a panel of more than 120 unrelated kinases (Kis > 5 μM). R547 inhibits tumor cell proliferation (IC50s ≤ 0.6 μM in vitro), inducing cell cycle arrest at G1 and G2 phases and apoptosis as well as reducing phosphorylation of the retinoblastoma protein. It also demonstrates antitumor activity in vivo in various human tumor xenograft models.

Technology Process of (4-Amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

There total 5 articles about (4-Amino-2-((1-(methylsulfonyl)piperidin-4-yl)amino)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone 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:

4-amino-1-methanesulfonylpiperidine (402927-97-3) + (4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone (741713-37-1) → Ro 4584820 (741713-40-6)

Guidance literature:

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone; With 3-chloro-benzenecarboperoxoic acid; In chloroform; at -15 ℃; for 1h;

4-amino-1-methanesulfonylpiperidine; In isopropyl alcohol; at 100 - 110 ℃; for 1h; microwave irradiation;

DOI:10.1021/jm0606138

Reference yield:

4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide (741712-36-7) → Ro 4584820 (741713-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

1.2: tetrahydrofuran; hexane / 2 h / -78 - -35 °C

2.1: m-CPBA / CHCl₃ / 1 h / -15 °C

2.2: propan-2-ol / 1 h / 100 - 110 °C / microwave irradiation

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; chloroform;

DOI:10.1021/jm0606138

Reference yield:

(1-methanesulfonyl-piperidin-4-yl)carbamic acid tert-butyl ester (287953-38-2) → Ro 4584820 (741713-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CF₃CO₂H / CH₂Cl₂ / 2 h / 20 °C

2.1: m-CPBA / CHCl₃ / 1 h / -15 °C

2.2: propan-2-ol / 1 h / 100 - 110 °C / microwave irradiation

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1021/jm0606138

upstream raw materials:

4-amino-1-methanesulfonylpiperidine

(4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide

(1-methanesulfonyl-piperidin-4-yl)carbamic acid tert-butyl ester

Refernces