4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone

Base Information

• Chemical Name: 4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone
• CAS No.: 306296-62-8
• Molecular Formula: C₂₇H₃₆F₃N₅O
• Molecular Weight: 503.611
• DSSTox Substance ID: DTXSID501101509
• Nikkaji Number: J1.872.553C
• Pharos Ligand ID: HHXS9NA74LG4
• ChEMBL ID: CHEMBL311795
• Mol file: 306296-62-8.mol

Synonyms:CHEMBL311795;4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone;SCHEMBL5076337;DTXSID501101509;BDBM50123435;(4,6-Dimethyl-5-pyrimidinyl)[4-methyl-4-[(3S)-3-methyl-4-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]-1-piperazinyl]-1-piperidinyl]methanone;(4,6-Dimethyl-pyrimidin-5-yl)-(4-methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidin-1-yl)-methanone;(4,6-dimethylpyrimidin-5-yl)-[4-methyl-4-[(3S)-3-methyl-4-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-1-piperidyl]methanone;1-(4,6-Dimethyl-pyrimidin-5-yl)-1-(4-methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidin-1-yl)-methanone;306296-62-8

Chemical Property of 4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 503.28719528
• Heavy Atom Count: 36
• Complexity: 738

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CN(CCN1C(C)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
• Isomeric SMILES: C[C@H]1CN(CCN1[C@@H](C)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C

Technology Process of 4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone

There total 8 articles about 4-[(3S)-4-[(S)-4-(Trifluoromethyl)-alpha-methylbenzyl]-3-methyl-piperazino]-4-methylpiperidino 4,6-dimethyl-5-pyrimidinyl ketone 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: 91.0%

C20H30F3N3*3ClH + 4,6-dimethylpyrimidine-5-carboxylic acid (157335-93-8) → (4,6-Dimethyl-pyrimidin-5-yl)-(4-methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidin-1-yl)-methanone (306296-62-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 45 ℃; for 18h;

Reference yield:

ethyl 2‐acetyl‐3‐methoxybut‐2‐enoate (69119-22-8) → (4,6-Dimethyl-pyrimidin-5-yl)-(4-methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidin-1-yl)-methanone (306296-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOEt / ethanol / Heating

2: alkaline solution

3: EDCI; HOBt; i-Pr₂NEt / CH₂Cl₂

With alkaline solution; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;

DOI:10.1016/S0960-894X(02)00918-6

Reference yield:

tert-butyl 2-acetyl-3-oxobutanoate (91179-57-6) → (4,6-Dimethyl-pyrimidin-5-yl)-(4-methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidin-1-yl)-methanone (306296-62-8)

Guidance literature:

Multi-step reaction with 4 steps

1: CsCO₃ / acetonitrile

2: NaOEt / ethanol / Heating

3: acidic solution

4: EDCI; HOBt; i-Pr₂NEt / CH₂Cl₂

With acidic solution; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0960-894X(02)00918-6

upstream raw materials:

4,6-dimethylpyrimidine-5-carboxylic acid

2-methyl-4-(4-methylpiperidin-4-yl)-1-[1-(4-trifluoromethylphenyl)ethyl]piperazine

ethyl 2‐acetyl‐3‐methoxybut‐2‐enoate

tert-butyl 2-acetyl-3-oxobutanoate

Refernces

• 1、 -. "Piperazine derivatives useful as CCR5 antagonists". Page column 86. . Retrieved 2010/02/05.