(+)-(R)-((E)-3-(2-Phenylpyrazolo(1,5-a)pyridin-3-yl)acryloyl)-2-piperidineethanol

Base Information

• Chemical Name: (+)-(R)-((E)-3-(2-Phenylpyrazolo(1,5-a)pyridin-3-yl)acryloyl)-2-piperidineethanol
• CAS No.: 121524-18-3
• Molecular Formula: C23H25 N3 O2
• Molecular Weight: 375.47
• DSSTox Substance ID: DTXSID001113375
• Nikkaji Number: J532.709A
• Wikidata: Q27077297
• Pharos Ligand ID: BDXCCMGJ3D5M
• ChEMBL ID: CHEMBL440115
• Mol file: 121524-18-3.mol

Synonyms:(+)-(R)-(1-(E)-3-(2-phenylpyrazolo(1,5-a)pyridin-3-yl)acryl)-2-piperidine ethanol;FK 453;FR 113452;FR 113453;FR113452;FR113453

Chemical Property of (+)-(R)-((E)-3-(2-Phenylpyrazolo(1,5-a)pyridin-3-yl)acryloyl)-2-piperidineethanol

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 15.15±0.10(Predicted)
• Flash Point: °C
• PSA: 57.84000
• Density: 1.21g/cm³
• LogP: 3.71590
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 375.19467705
• Heavy Atom Count: 28
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

(R-(E))-1-(1-OXO-3-(2-PHENYLPYRAZOLO(1,5-A)PYRIDIN-3-YL)-2-PROPENYL)-2-PIPERIDINEETHANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C(C1)CCO)C(=O)C=CC2=C3C=CC=CN3N=C2C4=CC=CC=C4
• Isomeric SMILES: C1CCN([C@H](C1)CCO)C(=O)/C=C/C2=C3C=CC=CN3N=C2C4=CC=CC=C4

Technology Process of (+)-(R)-((E)-3-(2-Phenylpyrazolo(1,5-a)pyridin-3-yl)acryloyl)-2-piperidineethanol

There total 18 articles about (+)-(R)-((E)-3-(2-Phenylpyrazolo(1,5-a)pyridin-3-yl)acryloyl)-2-piperidineethanol 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: 98.0%

C26H33N3O2Si → (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(2-hydroxyethyl)piperidine (121524-18-3)

Guidance literature:

With methanol; potassium carbonate;

Reference yield:

3-(2-phenylpyrazolo[1,5-a]-pyridin-3-yl)acrylic acid (137453-39-5) + N,N-bis(trimethylsilyl)acetamide (10416-58-7) + (2R)-2-(2-methoxyethyl)piperidine (68419-38-5) → (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(2-hydroxyethyl)piperidine (121524-18-3)

Guidance literature:

With hydrogenchloride; sodium hydroxide; thionyl chloride; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

2-phenylpyrazolo[1,5-a]pyridine (56983-95-0) → (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(2-hydroxyethyl)piperidine (121524-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / POCl₃

2: NaH / tetrahydrofuran

3: aq. NaOH / methanol

4: 1.) SOCl₂, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

With sodium hydroxide; thionyl chloride; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol;

DOI:10.1016/0960-894X(96)00368-X

upstream raw materials:

2(RS)-(2-hydroxyethyl)piperidine

3-(2-phenylpyrazolo[1,5-a]-pyridin-3-yl)acrylic acid

2-phenylpyrazolo[1,5-a]pyridine

2-phenyl-pyrazolo[1,5-a]pyridine-3-carbaldehyde

Downstream raw materials:

(2R)-1-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)-acryloyl]-2-(formylmethyl)piperidine