[4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone

Base Information

• Chemical Name: [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone
• CAS No.: 1315484-23-1
• Molecular Formula: C₂₀H₁₉N₅O
• Molecular Weight: 345.404
• Mol file: 1315484-23-1.mol

Synonyms:[4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone

Chemical Property of [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone

There total 9 articles about [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone 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: 57.0%

1-piperidin-4-yl-1,6-dihydro-imidazo[4,5-d]pyrrolo[2,3-b]-pyridine (1315484-16-2) + benzoic acid (65-85-0,8013-63-6) → [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone (1315484-23-1)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1021/jm300438j

Reference yield:

4-chloro-7-azaindole (55052-28-3) → [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone (1315484-23-1)

Guidance literature:

Multi-step reaction with 8 steps

1: dmap; triethylamine / dichloromethane / 20 °C

2: tetrabutylammonium nitrate; trifluoroacetic anhydride / dichloromethane / 23.5 h / -5 - 20 °C

3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 120 °C

4: iron; ammonium chloride / methanol; water / 4 h / Reflux

5: toluene-4-sulfonic acid / toluene / 2 h / Reflux

6: sodium hydroxide / methanol / 18 h / 20 °C

7: 20% palladium hydroxide on charcoal; ammonium formate / methanol / 8 h / Inert atmosphere; Reflux

8: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

With dmap; 20% palladium hydroxide on charcoal; ammonium formate; tetrabutylammonium nitrate; iron; ammonium chloride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; sodium hydroxide; In methanol; dichloromethane; water; isopropyl alcohol; toluene;

DOI:10.1021/jm300438j

Reference yield:

1-[1-(phenylmethyl)-piperidin-4-yl]-1,6-dihydro-imidazo-[4,5-d]pyrrolo[2,3-b]pyridine (1315484-14-0) → [4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(6H)-yl)-piperidin-1-yl]phenylmethanone (1315484-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 20% palladium hydroxide on charcoal; ammonium formate / methanol / 8 h / Inert atmosphere; Reflux

2: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

With dmap; 20% palladium hydroxide on charcoal; ammonium formate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane;

DOI:10.1021/jm300438j

upstream raw materials:

1-[1-(phenylmethyl)-piperidin-4-yl]-1,6-dihydro-imidazo-[4,5-d]pyrrolo[2,3-b]pyridine

1-piperidin-4-yl-1,6-dihydro-imidazo[4,5-d]pyrrolo[2,3-b]-pyridine

benzoic acid

1-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 -. "TRICYCLIC HETEROCYCLIC COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF". Page/Page column 189. . Retrieved 2011/08/04.