Benzamide, 4-(1-aminoethyl)-N-1H-pyrrolo(2,3-b)pyridin-4-yl-, (R)-

Base Information

• Chemical Name: Benzamide, 4-(1-aminoethyl)-N-1H-pyrrolo(2,3-b)pyridin-4-yl-, (R)-
• CAS No.: 199433-58-4
• Molecular Formula: C16H16N4O
• Molecular Weight: 280.32
• UNII: 00ALI1GAY2
• DSSTox Substance ID: DTXSID50173718
• Nikkaji Number: J2.643.058E
• Wikidata: Q27163266
• Pharos Ligand ID: ZG45S5C89F8L
• ChEMBL ID: CHEMBL571948
• Mol file: 199433-58-4.mol

Synonyms:4-((1R)-1-aminoethyl)-N-(1H-pyrrolo(2,3-b)pyridin-4-yl)benzamide;Y-33075;Y33075

Chemical Property of Benzamide, 4-(1-aminoethyl)-N-1H-pyrrolo(2,3-b)pyridin-4-yl-, (R)-

Chemical Property:

• Boiling Point: 444.644 °C at 760 mmHg
• PKA: 11.13±0.20(Predicted)
• Flash Point: 222.713 °C
• PSA: 83.80000
• Density: 1.327 g/cm³
• LogP: 3.60820
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 280.13241115
• Heavy Atom Count: 21
• Complexity: 367

Purity/Quality:

98%min ^*data from raw suppliers

Y-39983 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)C(=O)NC2=C3C=CNC3=NC=C2)N
• Isomeric SMILES: C[C@H](C1=CC=C(C=C1)C(=O)NC2=C3C=CNC3=NC=C2)N

Technology Process of Benzamide, 4-(1-aminoethyl)-N-1H-pyrrolo(2,3-b)pyridin-4-yl-, (R)-

There total 5 articles about Benzamide, 4-(1-aminoethyl)-N-1H-pyrrolo(2,3-b)pyridin-4-yl-, (R)- 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:

(R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide dihydrochloride (173897-44-4) → (R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide (199433-58-4)

Guidance literature:

With sodium hydroxide; In water; Cooling with ice;

Reference yield:

(R)-(+)-4-(1-benzyloxycarbonylaminoethyl)-benzoic acid (173898-15-2) → (R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide (199433-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 8 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: hydrogenchloride; 10% palladium hydroxide on charcoal; hydrogen / methanol / 1 h / 40 °C

4.1: sodium hydroxide / water / Cooling with ice

With hydrogenchloride; thionyl chloride; 10% palladium hydroxide on charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(R)-4-(1-benzyloxycarbonylaminoethyl)benzoic acid chloride (173897-73-9) → (R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide (199433-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 8 h / 20 °C

1.2: 0.5 h / 20 °C

2.1: hydrogenchloride; 10% palladium hydroxide on charcoal; hydrogen / methanol / 1 h / 40 °C

3.1: sodium hydroxide / water / Cooling with ice

With hydrogenchloride; 10% palladium hydroxide on charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; water; acetonitrile;

upstream raw materials:

(R)-(+)-4-(1-benzyloxycarbonylaminoethyl)-benzoic acid

(R)-4-(1-benzyloxycarbonylaminoethyl)benzoic acid chloride

(R)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide

(R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide dihydrochloride

Refernces

• 1、 -. "Agent for prophylaxis and treatment of glaucoma". . . Retrieved 2008/06/13.
• 2、 -. "Antitumor effect potentiators". . . Retrieved 2008/06/13.