Formoterol hemifumarate

Base Information

• Chemical Name: Formoterol hemifumarate
• CAS No.: 87833-61-2
• Deprecated CAS: 83536-10-1,87481-49-0,87833-61-2,87481-49-0,87833-61-2
• Molecular Formula: C₄H₄O₄*2C₁₉H₂₄N₂O₄
• Molecular Weight: 804.894
• European Community (EC) Number: 610-119-5
• UNII: P3T5QA5J9N
• DSSTox Substance ID: DTXSID5044239
• Wikidata: Q27132391
• NCI Thesaurus Code: C47540
• RXCUI: 236216
• ChEMBL ID: CHEMBL3184383
• Mol file: 87833-61-2.mol

Synonyms:3-formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarate;arformoterol;BD 40A;eformoterol;Foradil;formoterol;formoterol fumarate;formoterol fumarate, ((R*,R*)-(+-))-isomer;formoterol, ((R*,R*)-(+-))-isomer;Oxis

Chemical Property of Formoterol hemifumarate

Chemical Property:

• PSA: 168.91000
• LogP: 2.97550
• Solubility.: DMSO: 20 mg/mL, soluble
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 18
• Exact Mass: 804.35817311
• Heavy Atom Count: 58
• Complexity: 507

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O.CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.C(=C/C(=O)O)\C(=O)O
• Recent ClinicalTrials: Replication of the P04334 Asthma Trial in Healthcare Claims Data
• Recent EU Clinical Trials: CONNected Electronic Inhalers Asthma Control Trial 3 (“CONNECT 3”), a 24-Week Treatment, Multicenter, Open-Label, Randomized, Parallel Group Comparison Study of Standard of Care Treatment Versus the Budesonide/Formoterol Digihaler Digital System, to Optimize Outcomes in Adult Patients with Asthma
• Recent NIPH Clinical Trials: None

Technology Process of Formoterol hemifumarate

There total 19 articles about Formoterol hemifumarate 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: 83.68%

formoterol (128954-45-0,67346-49-0) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → formoterol fumarate (169375-55-7,87833-61-2)

Guidance literature:

In methanol; dimethyl sulfoxide; at 20 - 30 ℃; for 0.166667h;

Reference yield: 62.0%

N-[5-(2-{benzyl[2-(4-methoxyphenyl)-1-methylethyl]amino}-1-hydroxyethyl)-2-benzyloxyphenyl]formamide (43229-70-5) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → formoterol hemifumarate (87833-61-2)

Guidance literature:

N-[5-(2-{benzyl[2-(4-methoxyphenyl)-1-methylethyl]amino}-1-hydroxyethyl)-2-benzyloxyphenyl]formamide; With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃;

(2E)-but-2-enedioic acid; In isopropyl alcohol;

Reference yield:

[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine (43229-65-8) → N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-(4-methoxyphenyl)-1-methylethyl]-amino]ethyl]phenyl]formamide (43229-80-7,87833-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol / 20 °C / Inert atmosphere; Reflux

2.1: potassium carbonate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere

2.2: 255 / 24 h / 120 °C / Inert atmosphere

2.3: 25 °C / 2327.23 Torr / Inert atmosphere

3.1: isopropyl alcohol / 1 h / 25 °C / Inert atmosphere; Reflux

With potassium carbonate; In tetrahydrofuran; methanol; isopropyl alcohol;

upstream raw materials:

formoterol

(2E)-but-2-enedioic acid

[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine

2-(3-benzyloxy-4-nitrophenyl)oxirane

Refernces

• 1、 -. "The formoterol chiral intermediate resolution method". Paragraph 0082; 0083. . Retrieved 2017/08/31.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF HIGH PURITY FORMOTEROL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS". Page/Page column 20-21. . Retrieved 2010/11/30.