L-655,708

Base Information

• Chemical Name: L-655,708
• CAS No.: 130477-52-0
• Molecular Formula: C18H19N3O4
• Molecular Weight: 341.367
• UNII: L4BX842T8C
• DSSTox Substance ID: DTXSID901017625
• Nikkaji Number: J831.310E
• Wikipedia: L-655,708
• Wikidata: Q6456072
• Pharos Ligand ID: Q7P32PF933FG
• ChEMBL ID: CHEMBL52030
• Mol file: 130477-52-0.mol

Synonyms:(3H)L-655,708;L 655,708;L 655708;L-655,708;L-655708;L655708

Chemical Property of L-655,708

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.21E-13mmHg at 25°C
• Melting Point: 175-176 °C
• Refractive Index: 1.675
• Boiling Point: 584.4 °C at 760 mmHg
• PKA: 1.49±0.20(Predicted)
• Flash Point: 307.2 °C
• PSA: 73.66000
• Density: 1.42 g/cm³
• LogP: 2.28620
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: 6 mg/mL
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 341.13755610
• Heavy Atom Count: 25
• Complexity: 542

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-655,708 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=C2C3CCCN3C(=O)C4=C(N2C=N1)C=CC(=C4)OC
• Isomeric SMILES: CCOC(=O)C1=C2[C@@H]3CCCN3C(=O)C4=C(N2C=N1)C=CC(=C4)OC
• Uses: L-655,708 has been used as an α5 GABAA receptor inverse agonist to inhibit the discriminative stimulus of propofol in a dose-dependent manner.

Technology Process of L-655,708

There total 4 articles about L-655,708 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: 60.0%

Ethyl isocyanoacetate (2999-46-4) + (11aS)-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione (130477-46-2) → ethyl (S)-7-methoxy-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate (130477-52-0)

Guidance literature:

(11aS)-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione; With potassium tert-butylate; diethyl chlorophosphate; In tetrahydrofuran; at -20 - 20 ℃; for 4h; Inert atmosphere;

Ethyl isocyanoacetate; With potassium tert-butylate; at -20 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.11.045

Reference yield:

5-methoxy-2-nitro-benzoic acid (1882-69-5) → ethyl (S)-7-methoxy-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate (130477-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 20 °C

2.1: bis(trichloromethyl) carbonate; hydrogenchloride / water / 4 h / 20 °C

3.1: dimethyl sulfoxide / 2 h / 160 °C

4.1: potassium tert-butylate; diethyl chlorophosphate / tetrahydrofuran / 4 h / -20 - 20 °C / Inert atmosphere

4.2: 8 h / -20 - 20 °C / Inert atmosphere

With hydrogenchloride; bis(trichloromethyl) carbonate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; diethyl chlorophosphate; In tetrahydrofuran; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/j.ejmech.2016.11.045

Reference yield:

2-Amino-5-methoxybenzoic acid (6705-03-9) → ethyl (S)-7-methoxy-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate (130477-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bis(trichloromethyl) carbonate; hydrogenchloride / water / 4 h / 20 °C

2.1: dimethyl sulfoxide / 2 h / 160 °C

3.1: potassium tert-butylate; diethyl chlorophosphate / tetrahydrofuran / 4 h / -20 - 20 °C / Inert atmosphere

3.2: 8 h / -20 - 20 °C / Inert atmosphere

With hydrogenchloride; bis(trichloromethyl) carbonate; potassium tert-butylate; diethyl chlorophosphate; In tetrahydrofuran; water; dimethyl sulfoxide;

DOI:10.1016/j.ejmech.2016.11.045

upstream raw materials:

Ethyl isocyanoacetate

(11aS)-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione

5-methoxy-2-nitro-benzoic acid

2-Amino-5-methoxybenzoic acid

Refernces

• 1、 Li, Xiaoyan,Ma, Chunrong,He, Xiaohui,Yu, Jianming,Han, Dongmei,Zhang, Chunchun,Atack, John R.,Cook, James M.. "Studies in search of diazepam-insensitive subtype selective agents for GABA/Bz receptors". . p. 504 - 537. Retrieved 2007/10/03.