Benzenesulfonamide, N-[3-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin -6-yl]oxy]phenyl]-4-methyl-

Base Information

• Chemical Name: Benzenesulfonamide, N-[3-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin -6-yl]oxy]phenyl]-4-methyl-
• CAS No.: 850664-74-3
• Molecular Formula: C23H21N7O4S
• Molecular Weight: 491.53
• Mol file: 850664-74-3.mol

Synonyms:N-{3-[2-(4-amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yloxy]-phenyl}-4-methyl-benzenesulfonamide;

Chemical Property of Benzenesulfonamide, N-[3-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin -6-yl]oxy]phenyl]-4-methyl-

Chemical Property:

• PSA: 159.43000
• LogP: 5.71990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenesulfonamide, N-[3-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin -6-yl]oxy]phenyl]-4-methyl-

There total 11 articles about Benzenesulfonamide, N-[3-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin -6-yl]oxy]phenyl]-4-methyl- 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: 42.0%

2-{1-ethyl-6-[(3-{[(4-methylphenyl)sulfonyl]amino}phenyl)oxy]-1H-imidazo[4,5-c]pyridin-2-yl}-N-hydroxy-2-(hydroxyimino)ethanimidamide → N-(3-{[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-4-methylbenzenesulfonamide (850664-74-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; for 9h; Heating;

DOI:10.1021/jm060873p

Reference yield:

4-hydroxy-3-nitropyridine (5435-54-1) → N-(3-{[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-4-methylbenzenesulfonamide (850664-74-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / POCl₃ / toluene / 16 h / 110 °C

2: 80 percent / potassium t-butoxide; t-BuOOH / tetrahydrofuran; decane; liquid ammonia / 2 h / -35 °C

3: 74 percent / POCl₃ / toluene / 6 h / Heating

4: 83 percent / tetrahydrofuran; H₂O / 1 h

5: 96 percent / K₂CO₃ / dimethylformamide / 24 h / 100 °C

6: H₂ / Pd/C / methanol; tetrahydrofuran / 6 h / 3750.3 Torr

7: Et₃N; EDCl / D₂O / 15 - 20 °C

8: acetic acid / 5 h / Heating

9: aq. HCl; sodium nitrite / methanol / 28 h / 15 - 20 °C

10: 88 percent / hydroxylamine / tetrahydrofuran / 10 h / Heating

11: 42 percent / Et₃N / dioxane / 9 h / Heating

With hydrogenchloride; tert.-butylhydroperoxide; potassium tert-butylate; hydrogen; hydroxylamine; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; decane; ammonia; water; water-d2; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm060873p

Reference yield:

4-chloro-2-hydroxy-5-nitropyridine (850663-54-6) → N-(3-{[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-4-methylbenzenesulfonamide (850664-74-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 74 percent / POCl₃ / toluene / 6 h / Heating

2: 83 percent / tetrahydrofuran; H₂O / 1 h

3: 96 percent / K₂CO₃ / dimethylformamide / 24 h / 100 °C

4: H₂ / Pd/C / methanol; tetrahydrofuran / 6 h / 3750.3 Torr

5: Et₃N; EDCl / D₂O / 15 - 20 °C

6: acetic acid / 5 h / Heating

7: aq. HCl; sodium nitrite / methanol / 28 h / 15 - 20 °C

8: 88 percent / hydroxylamine / tetrahydrofuran / 10 h / Heating

9: 42 percent / Et₃N / dioxane / 9 h / Heating

With hydrogenchloride; hydrogen; hydroxylamine; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; water-d2; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm060873p

upstream raw materials:

4-chloro-2-hydroxy-5-nitropyridine

2-chloro-N-ethyl-5-nitro-4-pyridinamine

N-(3-{[5-amino-4-(ethylamino)-2-pyridinyl]oxy}phenyl)-4-methylbenzenesulfonamide

N-(3-{[4-(ethylamino)-5-nitro-2-pyridinyl]oxy}phenyl)-4-methylbenzenesulfonamide

Downstream raw materials:

GSK₂₆₉₉₆₂A

4-{6-[(3-aminophenyl)oxy]-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl}-furazan-3-amine