N-Formyl Desloratadine

Base Information

• Chemical Name: N-Formyl Desloratadine
• CAS No.: 117810-61-4
• Molecular Formula: C20H19ClN2O
• Molecular Weight: 338.83066
• Hs Code.: 2933399090
• UNII: 5TC65UK919
• ChEMBL ID: CHEMBL325909
• Nikkaji Number: J360.301F
• Mol file: 117810-61-4.mol

Synonyms:N-Formyl Desloratadine;117810-61-4;N-Formyldesloratadine;4-(13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidine-1-carbaldehyde;CHEMBL325909;5TC65UK919;11H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 1-piperidinecarboxaldehyde;1-Piperidinecarboxaldehyde, 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-;8-Chloro-6,11-dihydro-11-(N-formyl-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine;Formyl Loratadine;N-Formyl-desloratadine;UNII-5TC65UK919;SCHEMBL8876967;BDBM50007464;AKOS005141899;CCG-356576;CS-0168604;N-Formyl Desloratadine (Desloratadine Impurity);N-Formyl Desloratadine (Desloratadine Impurity D);4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carbaldehyde;4-{13-chloro-4-azatricyclo[9.4.0.0(3),]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carbaldehyde;4-{13-chloro-4-azatricyclo[9.4.0.0,pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carbaldehyde;8-Chloro-6,11-dihydro-11-(N-formyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;Desloratadine Related Compound F

Chemical Property of N-Formyl Desloratadine

Chemical Property:

• Melting Point: 147-149 °C
• Boiling Point: 543.2±50.0 °C(Predicted)
• PKA: 4.17±0.20(Predicted)
• PSA: 33.20000
• Density: 1.323±0.06 g/cm3(Predicted)
• LogP: 4.46150
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Very Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 338.1185909
• Heavy Atom Count: 24
• Complexity: 496

Purity/Quality:

98% ^*data from raw suppliers

N-FormylDesloratadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC(=C2)Cl)C(=C3CCN(CC3)C=O)C4=C1C=CC=N4
• Uses: N-Formyl Desloratadine is an impurity of Desloratadine (D290250), a nonsedating-type histamine H1-receptor antagonist.

Technology Process of N-Formyl Desloratadine

There total 10 articles about N-Formyl Desloratadine 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: 60.0%

carbon dioxide (124-38-9,18923-20-1) + descarboethoxyloratadine (100643-71-8) → N-formyldesloratadine (117810-61-4)

Guidance literature:

With hydrogen; In methanol; at 120 ℃; for 24h; under 30003 Torr; Autoclave;

DOI:10.1002/anie.202011260

Reference yield:

N-tert-butyl-3-methylpyridine-2-carboxamide (32998-95-1) → N-formyldesloratadine (117810-61-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) THF, -40 deg C

2: POCl₃ / Heating

3: 2.) aq. HCl / 1.) THF, reflux

4: CF₃SO₃H / Heating

5: Et₃N / toluene / Heating

6: aq. KOH / Heating

7: C₅H₅N / CH₂Cl₂

With pyridine; hydrogenchloride; potassium hydroxide; n-butyllithium; trifluorormethanesulfonic acid; triethylamine; trichlorophosphate; In dichloromethane; toluene;

DOI:10.1021/jm00105a069

Reference yield:

3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile (31255-57-9) → N-formyldesloratadine (117810-61-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) aq. HCl / 1.) THF, reflux

2: CF₃SO₃H / Heating

3: Et₃N / toluene / Heating

4: aq. KOH / Heating

5: C₅H₅N / CH₂Cl₂

With pyridine; hydrogenchloride; potassium hydroxide; trifluorormethanesulfonic acid; triethylamine; In dichloromethane; toluene;

DOI:10.1021/jm00105a069

upstream raw materials:

descarboethoxyloratadine

formic acid ethyl ester

N-tert-butyl-3-methylpyridine-2-carboxamide

3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile

Refernces

• 1、 Liu, Hangyu,Mei, Qingqing,Xu, Qingling,Song, Jinliang,Liu, Huizhen,Han, Buxing. "Synthesis of formamides containing unsaturated groups by: N -formylation of amines using CO2 with H2". supporting information. p. 196 - 201. Retrieved 2017/08/15.
• 2、 Piwinski, John J.,Wong, Jesse K.,Green, Michael J.,Ganguly, Ashit K.,Billah, M. Motasim,et al.. "Dual Antagonists of Platelet Activating Factor and Histamine. Identification of Structural Requirements for Dual Activity of N-Acyl-4-(5,6-dihydro-11H-benzocycloheptapyridin-11-ylidene)piperidines". . p. 457 - 461. Retrieved 2007/10/02.