4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester

Base Information

• Chemical Name: 4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester
• CAS No.: 100827-83-6
• Molecular Formula: C19H17ClN4O2S
• Molecular Weight: 400.889
• DSSTox Substance ID: DTXSID30546345
• Mol file: 100827-83-6.mol

Synonyms:100827-83-6;4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester;Methyl 3-[7-(2-chlorophenyl)-13-methyl-3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-4-yl]propanoate;6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic acid, 4-(2-chlorophenyl)-9-methyl-, methyl ester;SCHEMBL8928557;DTXSID30546345;AKOS030240977;Methyl 3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]propanoate

Chemical Property of 4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester

Chemical Property:

• Vapor Pressure: 3.93E-14mmHg at 25°C
• Boiling Point: 595.2°C at 760 mmHg
• Flash Point: 313.7°C
• PSA: 97.61000
• Density: 1.45g/cm³
• LogP: 3.18280
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 400.0760747
• Heavy Atom Count: 27
• Complexity: 592

Purity/Quality:

98%min ^*data from raw suppliers

4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C2N1C3=C(C=C(S3)CCC(=O)OC)C(=NC2)C4=CC=CC=C4Cl
• Uses: Brotizolam derivative; a thienotriazolodiazepines as platelet activating factor antagonist.

Technology Process of 4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester

There total 12 articles about 4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-2-propanoic Acid Methyl Ester 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: 80.0%

Triethyl orthoacetate (78-39-7) + 3-[5-(2-Chloro-phenyl)-2-hydrazono-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-7-yl]-propionic acid methyl ester (100827-84-7) → 2-(2-carbomethoxyethyl)-4-(2-chlorophenyl)-9-methyl-6H-thieno-<3,2-f><1,2,4>triazolo-<4,3-a><1,4>-diazepine (100827-83-6)

Guidance literature:

at 80 ℃; for 1h;

DOI:10.1002/jps.2600741205

Reference yield:

diethyl 2-(3-oxo-propyl)malonate (19515-61-8) → 2-(2-carbomethoxyethyl)-4-(2-chlorophenyl)-9-methyl-6H-thieno-<3,2-f><1,2,4>triazolo-<4,3-a><1,4>-diazepine (100827-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 74 percent / sulfur, Et₃N / dimethylformamide / 3 h / 60 - 70 °C

2: 30 g / KOH, water / methanol / 2 h / Heating

3: 45 percent / H₂SO₄ / 18 h / Ambient temperature

4: 92 percent / aq. NaHCO₃ / toluene / 1.5 h / 40 - 50 °C

5: 25 g / NH₃ / ethyl acetate / 3 h / Ambient temperature

6: 52 percent / silica gel / toluene / Heating

7: P₂S₅, NaHCO₃ / bis-(2-methoxy-ethyl) ether / 3 h / 70 - 80 °C

8: 6 g / hydrazine / tetrahydrofuran / 0.5 h / 45 - 80 °C

9: 80 percent / 1 h / 80 °C

With potassium hydroxide; tetraphosphorus decasulfide; sulfuric acid; ammonia; water; silica gel; sodium hydrogencarbonate; sulfur; triethylamine; hydrazine; In tetrahydrofuran; methanol; diethylene glycol dimethyl ether; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1002/jps.2600741205

Reference yield:

2-Chlorobenzoyl acetonitrile (40018-25-5) → 2-(2-carbomethoxyethyl)-4-(2-chlorophenyl)-9-methyl-6H-thieno-<3,2-f><1,2,4>triazolo-<4,3-a><1,4>-diazepine (100827-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 74 percent / sulfur, Et₃N / dimethylformamide / 3 h / 60 - 70 °C

2: 30 g / KOH, water / methanol / 2 h / Heating

3: 45 percent / H₂SO₄ / 18 h / Ambient temperature

4: 92 percent / aq. NaHCO₃ / toluene / 1.5 h / 40 - 50 °C

5: 25 g / NH₃ / ethyl acetate / 3 h / Ambient temperature

6: 52 percent / silica gel / toluene / Heating

7: P₂S₅, NaHCO₃ / bis-(2-methoxy-ethyl) ether / 3 h / 70 - 80 °C

8: 6 g / hydrazine / tetrahydrofuran / 0.5 h / 45 - 80 °C

9: 80 percent / 1 h / 80 °C

With potassium hydroxide; tetraphosphorus decasulfide; sulfuric acid; ammonia; water; silica gel; sodium hydrogencarbonate; sulfur; triethylamine; hydrazine; In tetrahydrofuran; methanol; diethylene glycol dimethyl ether; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1002/jps.2600741205

upstream raw materials:

Triethyl orthoacetate

3-[5-(2-Chloro-phenyl)-2-hydrazono-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-7-yl]-propionic acid methyl ester

diethyl 2-(3-oxo-propyl)malonate

2-Chlorobenzoyl acetonitrile

Downstream raw materials:

2-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]-ethane-1-carboxylic acid