2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Base Information

Chemical Name:2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
CAS No.:189392-52-7
Molecular Formula:C₂₁H₁₉ClN₄OS
Molecular Weight:410.927
Hs Code.:

Synonyms:2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

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Chemical Property of 2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

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Technology Process of 2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

There total 12 articles about 2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-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: 81.0%

: 2-chloro-5,11-dihydro-11-ethyl-8-[(phenylthio)-methyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

: 74-88-4
methyl iodide

: 189392-52-7
2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Guidance literature:: 2-chloro-5,11-dihydro-11-ethyl-8-[(phenylthio)-methyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 50 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.3762/bjoc.5.36

Reference yield: 62.0%

: 108-98-5
thiophenol

: 189391-90-0
2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

: 189392-52-7
2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Guidance literature:: In N,N-dimethyl-formamide;

Reference yield:

: 62476-56-6
3-amino-2,6-dichloropyridine

: 189392-52-7
2-chloro-5,11-dihydro-11-ethyl-8-{(phenyl)thiomethyl}-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / pyridine / dioxane; cyclohexane / 16 h

2: 60 percent / xylene / 6 h / 165 °C

3: 88 percent / Br₂, KOAc, AcOH / 0.25 h

4: 92 percent / sodium hexamethyldisilazide, pyridine / tetrahydrofuran / 0.17 h / 50 °C

5: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, RT, 1.5 h

6: 100 percent / (Ph₃P)4Pd / dimethylformamide / 2.5 h / 90 °C

7: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, MeOH, from -78 deg C to RT, 2.) CH₂Cl₂, MeOH, RT

8: 89 percent / NaBH₄, H₂O / tetrahydrofuran / 0.5 h

9: 93 percent / SOCl₂, Et₃N / CHCl₃ / 0.5 h

10: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, 18 h

With pyridine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; 2,3-dimercapto-succinic acid; water; bromine; potassium acetate; sodium hexamethyldisilazane; sodium hydride; ozone; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; chloroform; cyclohexane; N,N-dimethyl-formamide; xylene;
DOI:10.1021/jm9707030