7-(3-Amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Base Information

• Chemical Name: 7-(3-Amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS No.: 132832-30-5
• Molecular Formula: C16H17FN4O3
• Molecular Weight: 332.3296
• DSSTox Substance ID: DTXSID90927838
• Nikkaji Number: J631.737E
• Wikidata: Q82902537
• ChEMBL ID: CHEMBL132632
• Mol file: 132832-30-5.mol

Synonyms:7-(3(R)-amino-2(S)-methyl-1-azetidinyl)-1 cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-(3-amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;E 4695;E-4695;E4695

Chemical Property of 7-(3-Amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.84E-14mmHg at 25°C
• Boiling Point: 574.6°Cat760mmHg
• Flash Point: 301.3°C
• Density: 1.538g/cm³
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 332.12846858
• Heavy Atom Count: 24
• Complexity: 608

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CN1C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F)N
• Isomeric SMILES: C[C@H]1[C@@H](CN1C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F)N

Technology Process of 7-(3-Amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

There total 2 articles about 7-(3-Amino-2-methyl-1-azetidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid 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: 85.0%

1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (132235-01-9) + (2S,3R)-3-amino-2-methylazetidine dihydrochloride → 7-<(2S,3R)-3-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (132832-30-5)

Guidance literature:

With pyridine; triethylamine; for 3h; Heating;

DOI:10.1021/jm00007a017

Reference yield:

→ 7-<(2S,3R)-3-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (132832-30-5)

Guidance literature:

Reference yield: 97.0%

7-<(2S,3R)-3-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (132832-30-5) + (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester (3401-36-3) → 7-<(2S,3R)-3-N-CBZ-Ala-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (147906-13-6)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1021/jm00007a017

upstream raw materials:

1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Downstream raw materials:

7-<(2S,3R)-3-N-CBZ-D-Ala-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid

7-<(2S,3R)-3-N-CBZ-Ala-amino-2-methyl-1-azetidinyl>-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Refernces

• 1、 -. "Substituted azetidinylpyridone naphthyridine carboxylic acid derivatives and their application as medical products". . . Retrieved 2008/06/13.