1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one

Base Information

• Chemical Name: 1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one
• CAS No.: 112175-39-0
• Molecular Formula: C15H13N3O
• Molecular Weight: 251.288
• DSSTox Substance ID: DTXSID60550793
• Nikkaji Number: J558.239C
• Mol file: 112175-39-0.mol

Synonyms:112175-39-0;SCHEMBL7091681;DTXSID60550793;1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one

Chemical Property of 1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 251.105862047
• Heavy Atom Count: 19
• Complexity: 374

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CN=C(C2=C1C=NC=C2)C3=CC=CC=C3

Technology Process of 1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one

There total 13 articles about 1-Methyl-5-phenyl-1,3-dihydro-2H-pyrido[3,4-e][1,4]diazepin-2-one 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:

pyridin-3-ylamine (462-08-8) → 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido<3,4-e>-1,4-diazepin-2-one (112175-39-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / 2-methyl-propan-2-ol / 2 h / 80 °C

2: 1.) tert-butyllithium / 1.) pentane, THF, -78 deg C, 15 m, -20 deg C, 3 h, 2.) THF, 25 deg C

3: 97 percent / trifluoroacetic acid / 1,2-dichloro-ethane / 3.5 h / 25 °C

4: 1.) 1,1'-bis-<6-(trifluoromethyl)benzotriazolyl> oxalate (BTBO), pyridine, 2.) triethylamine / 1.) acetonitrile, 2 h, 25 deg C, 2.) THF, 25 deg C, 6 h

5: 89 percent / 1N trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 25 °C

6: 1.) 50percent NaH in oil / 1.) DMF, 0 deg C, 25 m, 2.) ether, 0 deg C, 30 m

With pyridine; 1,1'-bis[6-(trifluoromethyl)benzotriazolyl] oxalate; tert.-butyl lithium; sodium hydride; triethylamine; trifluoroacetic acid; In 1,2-dichloro-ethane; tert-butyl alcohol;

DOI:10.1139/v87-193

Reference yield:

N-(pyridin-3-yl)pivalamide (70298-88-3) → 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido<3,4-e>-1,4-diazepin-2-one (112175-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 15 m, 0 deg C, 3 h, 2.) THF, 25 deg C

2: 94 percent / 5 N HCl / aq. ethanol / 6 h / Heating

3: 1.) 1,1'-bis-<6-(trifluoromethyl)benzotriazolyl> oxalate (BTBO), pyridine, 2.) triethylamine / 1.) acetonitrile, 2 h, 25 deg C, 2.) THF, 25 deg C, 6 h

4: 89 percent / 1N trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 25 °C

5: 1.) 50percent NaH in oil / 1.) DMF, 0 deg C, 25 m, 2.) ether, 0 deg C, 30 m

With pyridine; hydrogenchloride; n-butyllithium; 1,1'-bis[6-(trifluoromethyl)benzotriazolyl] oxalate; sodium hydride; triethylamine; trifluoroacetic acid; In ethanol; 1,2-dichloro-ethane;

DOI:10.1139/v87-193

Reference yield:

3-(tert-butoxycarbonylamino)pyridine (56700-70-0) → 1,3-dihydro-1-methyl-5-phenyl-2H-pyrido<3,4-e>-1,4-diazepin-2-one (112175-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) tert-butyllithium / 1.) pentane, THF, -78 deg C, 15 m, -20 deg C, 3 h, 2.) THF, 25 deg C

2: 97 percent / trifluoroacetic acid / 1,2-dichloro-ethane / 3.5 h / 25 °C

3: 1.) 1,1'-bis-<6-(trifluoromethyl)benzotriazolyl> oxalate (BTBO), pyridine, 2.) triethylamine / 1.) acetonitrile, 2 h, 25 deg C, 2.) THF, 25 deg C, 6 h

4: 89 percent / 1N trifluoroacetic acid / 1,2-dichloro-ethane / 6 h / 25 °C

5: 1.) 50percent NaH in oil / 1.) DMF, 0 deg C, 25 m, 2.) ether, 0 deg C, 30 m

With pyridine; 1,1'-bis[6-(trifluoromethyl)benzotriazolyl] oxalate; tert.-butyl lithium; sodium hydride; triethylamine; trifluoroacetic acid; In 1,2-dichloro-ethane;

DOI:10.1139/v87-193

upstream raw materials:

1,3-dihydro-5-phenyl-2H-pyrido<3,4-e>-1,4-diazepin-2-one

methyl iodide

pyridin-3-ylamine

N,N-diethylbenzamide