N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide

Base Information

• Chemical Name: N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide
• CAS No.: 125867-26-7
• Molecular Formula: C₁₇H₂₀N₂O₂
• Molecular Weight: 284.358
• DSSTox Substance ID: DTXSID301176405
• Mol file: 125867-26-7.mol

Synonyms:N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide;125867-26-7;SCHEMBL9846978;DTXSID301176405;N-[3-(hydroxy-phenylmethyl)pyridin-4-yl]-2,2-dimethylpropanamide;N-[3-(Hydroxyphenylmethyl)-4-pyridinyl]-2,2-dimethylpropanamide;N-[3-[hydroxy(phenyl)methyl]pyridin-4-yl]-2,2-dimethylpropanamide;N-[3-(hydroxy-phenyl-methyl)-pyridin-4-yl]-2,2-dimethyl-propionamide

Chemical Property of N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 284.152477885
• Heavy Atom Count: 21
• Complexity: 345

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)NC1=C(C=NC=C1)C(C2=CC=CC=C2)O

Technology Process of N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide

There total 4 articles about N-(3-(hydroxy(phenyl)methyl)pyridin-4-yl)pivalamide 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: 90.0%

4-N-pivaloylaminopyridine (70298-89-4) + benzaldehyde (100-52-7) → N-[3-[hydroxy(phenyl)methyl]pyrydin-4-yl]-2,2-dimethylpropanamide (125867-26-7)

Guidance literature:

4-N-pivaloylaminopyridine; With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 - -20 ℃; Inert atmosphere; Schlenk technique;

benzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules26154473

Reference yield:

4-aminopyridine (504-24-5) + pivaloyl chloride (3282-30-2) → N-[3-[hydroxy(phenyl)methyl]pyrydin-4-yl]-2,2-dimethylpropanamide (125867-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / Inert atmosphere; Schlenk technique

2.1: tert.-butyl lithium / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere; Schlenk technique

2.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique

With tert.-butyl lithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.3390/molecules26154473

Reference yield:

4-aminopyridine (504-24-5) → N-[3-[hydroxy(phenyl)methyl]pyrydin-4-yl]-2,2-dimethylpropanamide (125867-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / diethyl ether; hexane / 2.25 h / -78 - -24 °C

2.2: -78 - 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; triethylamine; In diethyl ether; hexane; dichloromethane;

upstream raw materials:

4-N-pivaloylaminopyridine

benzaldehyde

4-aminopyridine

pivaloyl chloride

Downstream raw materials:

(4-aminopyridin-3-yl)(phenyl)methanone

10-phenyl-6,7,8,9-tetrahydrobenzo<1,6>naphthyridine

4-phenyl-1,2-dihydropyrido<4,3-d>-2-pyrimidinone

phenyl (4-pivaloylamino-3-pyridyl) ketone

Refernces

• 1、 -. "PROTEIN KINASE INHIBITORS". Page/Page column 18. . Retrieved 2015/01/09.
• 2、 Martínez-Viturro, Carlos M.,Domínguez, Domingo. "Synthesis of aza analogues of the anticancer agent batracylin". . p. 4707 - 4710. Retrieved 2008/03/13.