(3S)-3-(6-Methoxy-3-pyridyl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid

Base Information

• Chemical Name: (3S)-3-(6-Methoxy-3-pyridyl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid
• CAS No.: 227963-15-7
• Molecular Formula: C₂₃H₂₉N₅O₄
• Molecular Weight: 439.514
• European Community (EC) Number: 836-017-2
• UNII: 1JL033A2D0
• DSSTox Substance ID: DTXSID901347137
• Nikkaji Number: J1.969.455K
• Wikidata: Q27252505
• Pharos Ligand ID: X4X9Z8VHH79H
• ChEMBL ID: CHEMBL145085
• Mol file: 227963-15-7.mol

Synonyms:3-(6-methoxypyridin-3-yl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro(1,8)naphthyridin-2-yl)propyl)imidazolidin-1-yl)propionic acid;3-(6-methoxypyridin-3-yl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-(1,8)naphthyridin-2-yl)propyl)imidazolidin-1-yl)propionic acid;L-000845704;MK-0429;MOTNI-propionic acid

Chemical Property of (3S)-3-(6-Methoxy-3-pyridyl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid

Chemical Property:

• Melting Point: 122 °C
• Boiling Point: 735.5±60.0 °C(Predicted)
• Density: 1.36±0.1 g/cm3(Predicted)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 439.22195442
• Heavy Atom Count: 32
• Complexity: 650

Purity/Quality:

97% ^*data from raw suppliers

MK-0429 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=NC=C(C=C1)C(CC(=O)O)N2CCN(C2=O)CCCC3=NC4=C(CCCN4)C=C3
• Isomeric SMILES: COC1=NC=C(C=C1)[C@H](CC(=O)O)N2CCN(C2=O)CCCC3=NC4=C(CCCN4)C=C3
• Recent ClinicalTrials: Proof of Concept (Bone Resorption/Bone Mineral Density) Study (0429-005)

Technology Process of (3S)-3-(6-Methoxy-3-pyridyl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid

There total 46 articles about (3S)-3-(6-Methoxy-3-pyridyl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic 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: 93.0%

3(S)-(6-methoxypyridin-3-yl)-3-{2-oxo-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)propyl]imidazolidin-1-yl}propionic acid ethyl ester (227963-56-6) → (S)-3-(6-methoxypyridin-3-yl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid (227963-15-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 16h;

DOI:10.1021/jm030306r

Reference yield: 80.0%

(3S)-3-(6-methoxypyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-2,3-dihydro-1H-imidazol-1-yl}propanoic acid (339555-50-9) → (S)-3-(6-methoxypyridin-3-yl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid (227963-15-7)

Guidance literature:

With sodium hydroxide; hydrogen; palladium dihydroxide; at 80 ℃; for 18h; under 6205.78 Torr;

DOI:10.1021/jo030297u

Reference yield:

2-Aminonicotinaldehyde (7521-41-7) → (S)-3-(6-methoxypyridin-3-yl)-3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid (227963-15-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / NaOH / ethanol; H₂O / 1 h / 20 °C

2: 92 percent / H₂ / PtO₂ / ethanol / 18 h / 20 °C / 760 Torr

3: aq. HCl / 2.5 h / 85 °C

4: aq. NaOH / tetrahydrofuran / 20 °C

5: 89 percent / H₂; aq. NH₄OH / Raney Ni / 16 h / 50 °C / 2068.59 Torr

6: Et₃N / tetrahydrofuran; butan-2-ol / 3 h / 45 °C

7: aq. H₂SO₄ / tetrahydrofuran; butan-2-ol / 18 h / 20 °C

8: 86 percent / aq. H₂SO₄ / isopropyl acetate / 3 h / 40 °C

9: 80 percent / H₂; aq. NaOH / Pd(OH)2/C / 18 h / 80 °C / 6205.78 Torr

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; triethylamine; platinum(IV) oxide; palladium dihydroxide; nickel; In tetrahydrofuran; ethanol; Isopropyl acetate; water; iso-butanol; 1: Friedlaender reaction / 4: Horner-Emmons reaction;

DOI:10.1021/jo030297u

upstream raw materials:

3(S)-(6-methoxypyridin-3-yl)-3-{2-oxo-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)propyl]imidazolidin-1-yl}propionic acid ethyl ester

(3S)-3-(6-methoxypyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-2,3-dihydro-1H-imidazol-1-yl}propanoic acid

3-(6-methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-imidazolidin-1-yl}-propionic acid tert-butyl ester

2-Aminonicotinaldehyde