1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)-

Base Information

• Chemical Name: 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)-
• CAS No.: 205678-31-5
• Molecular Formula: C₂₂H₂₄F₃N₃O₄
• Molecular Weight: 451.445
• UNII: HG7MY8V9AA
• Nikkaji Number: J3.297.428G
• ChEMBL ID: CHEMBL86992
• Mol file: 205678-31-5.mol

Synonyms:205678-31-5;SB273005;SB-273005;HG7MY8V9AA;CHEMBL86992;1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)-;2-[(4S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-4,5-dihydro-1H-2-benzazepin-4-yl]acetic acid;(S)-2-(8-(2-(6-(Methylamino)pyridin-2-yl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)acetic acid;UNII-HG7MY8V9AA;SCHEMBL244675;BDBM50083763;s7540;CCG-269246;NCGC00386438-01;HY-19307;CS-0015050;A924365;(S)-8-[2-[6-(methylamino)pyridin-2-yl]-1-ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic Acid;[(S)-8-[2-(6-Methylamino-pyridin-2-yl)-ethoxy]-3-oxo-2-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-acetic acid;[8-[2-(6-Methylamino-pyridin-2-yl)-ethoxy]-3-oxo-2-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-acetic acid

Chemical Property of 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)-

Chemical Property:

• Boiling Point: 662.9±55.0 °C(Predicted)
• PKA: 4.32±0.10(Predicted)
• Density: 1.321±0.06 g/cm3(Predicted)
• Solubility.: Soluble in DMSO
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 451.17189074
• Heavy Atom Count: 32
• Complexity: 648

Purity/Quality:

99%+, ^*data from raw suppliers

SB273005 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNC1=CC=CC(=N1)CCOC2=CC3=C(CC(C(=O)N(C3)CC(F)(F)F)CC(=O)O)C=C2
• Isomeric SMILES: CNC1=CC=CC(=N1)CCOC2=CC3=C(C[C@H](C(=O)N(C3)CC(F)(F)F)CC(=O)O)C=C2

Technology Process of 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)-

There total 13 articles about 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-8-(2-(6-(methylamino)-2-pyridinyl)ethoxy)-3-oxo-2-(2,2,2-trifluoroethyl)-, (4S)- 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: 82.0%

methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]-1-ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (205677-86-7) → (4S)-2,3,4,5-tetrahydro-8-[2-[6-(methylamino)-2-pyridinyl]ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-1H-2-benzazepine-4-acetic acid (205678-31-5)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1021/jm990446u

Reference yield:

2-Amino-6-methylpyridine (1824-81-3) → (4S)-2,3,4,5-tetrahydro-8-[2-[6-(methylamino)-2-pyridinyl]ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-1H-2-benzazepine-4-acetic acid (205678-31-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / 50 °C

2.1: 87 percent / NaH / dimethylformamide

3.1: 100 percent / LDA / tetrahydrofuran / 0 °C

4.1: 100 percent / LiBH₄ / tetrahydrofuran / Heating

5.1: HCl; anisole / dioxane

5.2: HCO₂H / ethyl acetate

5.3: 52 percent / aq. NH₃

6.1: 91 percent / Ph₃P; DIAD / tetrahydrofuran

7.1: 82 percent / 1.0N aq. NaOH / methanol

With hydrogenchloride; sodium hydroxide; lithium borohydride; di-isopropyl azodicarboxylate; sodium hydride; methoxybenzene; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Methylation / 3.1: Condensation / 4.1: Reduction / 5.1: Hydrolysis / 5.2: Hydrolysis / 5.3: Hydrolysis / 6.1: Mitsunobu reaction / 7.1: Hydrolysis;

DOI:10.1021/jm990446u

Reference yield:

2-methylamino-6-(2-hydroxyethyl)pyridine (205676-87-5) → (4S)-2,3,4,5-tetrahydro-8-[2-[6-(methylamino)-2-pyridinyl]ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-1H-2-benzazepine-4-acetic acid (205678-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Ph₃P; DIAD / tetrahydrofuran

2: 82 percent / 1.0N aq. NaOH / methanol

With sodium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; 1: Mitsunobu reaction / 2: Hydrolysis;

DOI:10.1021/jm990446u

upstream raw materials:

methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]-1-ethoxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

2-Amino-6-methylpyridine

2-methylamino-6-(2-hydroxyethyl)pyridine

2-(tert-butoxycarbonylamino)-6-picoline

Refernces

• 1、 -. "PROCESS AND INTERMEDIATES FOR PREPARING BENZAZEPINES". Page 28-28; 40-41. . Retrieved 2010/02/09.
• 2、 Miller, William H.,Alberts, Doreen P.,Bhatnagar, Pradip K.,Bondinell, William E.,Callahan, James F.,Calvo, Raul R.,Cousins, Russell D.,Erhard, Karl F.,Heerding, Dirk A.,Keenan, Richard M.,Kwon, Chet,Manley, Peter J.,Newlander, Kenneth A.,Ross, Stephen T.,Samanen, James M.,Uzinskas, Irene N.,Venslavsky, Joseph W.,Yuan, Catherine C. -K,Haltiwanger, R. Curtis,Gowen, Maxine,Hwang, Shing-Mei,James, Ian E.,Lark, Michael W.,Rieman, David J.,Stroup, George B.,Azzarano, Leonard M.,Salyers, Kevin L.,Smith, Brian R.,Ward, Keith W.,Johanson, Kyung O.,Huffman, William F.. "Discovery of orally active nonpeptide vitronectin receptor antagonists based on a 2-benzazepine Gly-Asp mimetic [2]". . p. 22 - 26. Retrieved 2007/10/03.