10-Deazaaminopterin

Base Information

• Chemical Name: 10-Deazaaminopterin
• CAS No.: 52454-37-2
• Molecular Formula: C20H21 N7 O5
• Molecular Weight: 439.431
• Hs Code.: 2933990090
• UNII: PXJ16PPE04
• Nikkaji Number: J362.080H
• Pharos Ligand ID: JNZW8TRV5LHW
• ChEMBL ID: CHEMBL293263
• Mol file: 52454-37-2.mol

Synonyms:10-deaza-aminopterin;10-deazaaminopterin;10-deazaaminopterin hydrochloride;10-deazaaminopterin monohydrochloride;10-deazaaminopterin, sodium salt;10-deazaminopterin

Chemical Property of 10-Deazaaminopterin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 207.30000
• Density: 1.512g/cm³
• LogP: 1.97050
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 439.16041680
• Heavy Atom Count: 32
• Complexity: 673

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC2=CN=C3C(=N2)C(=NC(=N3)N)N)C(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC(=CC=C1CCC2=CN=C3C(=N2)C(=NC(=N3)N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O
• Uses: 10-Deazaminopterin inhibits neutrophil chemotaxis and superoxide generation. Pralatrexate impurity.

Technology Process of 10-Deazaaminopterin

There total 23 articles about 10-Deazaaminopterin 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:

(S)-2-{4-[2-(2,4-Diamino-pteridin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester (80577-71-5) → 10-deazaaminopterin (52454-37-2)

Guidance literature:

With sodium hydroxide; In ethanol; at 25 - 55 ℃; for 20.5h; Yield given;

DOI:10.1021/jm00177a022

Reference yield:

diethyl 4-formylbenzoyl-L-glutamate (56277-36-2) → 10-deazaaminopterin (52454-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / various solvent(s) / 17 h / 25 °C

2: H₂ / Pt / acetic acid / 20 °C / 760 Torr

3: 1 N aq. NaOH / ethanol / 20.5 h / 25 - 55 °C

With sodium hydroxide; hydrogen; sodium methylate; platinum; In ethanol; acetic acid;

DOI:10.1021/jm00177a022

Reference yield:

6-bromomethyl-2,4-diaminopteridine hydrobromide (52853-40-4) → 10-deazaaminopterin (52454-37-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Me₂NAc / 1.5 h / 60 - 63 °C

2: NaOMe / various solvent(s) / 17 h / 25 °C

3: H₂ / Pt / acetic acid / 20 °C / 760 Torr

4: 1 N aq. NaOH / ethanol / 20.5 h / 25 - 55 °C

With sodium hydroxide; N,N-dimethyl acetamide; hydrogen; sodium methylate; platinum; In ethanol; acetic acid;

DOI:10.1021/jm00177a022

upstream raw materials:

(S)-2-{4-[2-(2,4-Diamino-pteridin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester

4-<(2,4-diaminopteridin-6-yl)ethyl>benzoic acid

1-amino-4-(p-carbomethoxyphenyl)-2-butanone oxime

4-[2-(2,4-Diamino-7,8-dihydro-pteridin-6-yl)-ethyl]-benzoic acid

Refernces

• 1、 Nair, M. G.. "Folate Analogues. 24. Syntheses of the Antitumor Agents 10-Deazaaminopterin (10-DAAM) and 10-Ethyl-10-deazaaminopterin (10-EDAAM)". . p. 1879 - 1884. Retrieved 2007/10/02.
• 2、 Piper, James R.,Montgomery, John A.. "Convenient Synthesis of 10-Deazaaminopterin via a Pteridine Ylide". . p. 320 - 321. Retrieved 2007/10/02.