1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol

Base Information

• Chemical Name: 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol
• CAS No.: 129655-59-0
• Molecular Formula: C13H17N3O
• Molecular Weight: 0.00000
• Mol file: 129655-59-0.mol

Synonyms:

Chemical Property of 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol

Chemical Property:

• Melting Point: 110-112°C
• Boiling Point: 441.5±40.0 °C(Predicted)
• PKA: 14.67±0.29(Predicted)
• PSA: 0.00000
• Density: 1.246±0.06 g/cm3(Predicted)
• LogP: 0.00000
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98.5% ^*data from raw suppliers

1-[(3-Amino-4-quinolinyl)amino]-2-methyl-2-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[(3-Amino-4-quinolinyl)amino]-2-methyl-2-propanol is an intermediate in synthesizing Resiquimod-d5 (R144682), an isotope labelled Resiquimod (R144680) which is an imidazoquinoline derivative that acts as an immune response modifier. Resiquimod shows antitumor and antiviral activity and is used in the treatment of skin lesions such as herpes simplex virus. Resiquimod is a toll-like receptor 9 (TLR7) agonist.

Technology Process of 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol

There total 6 articles about 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol 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: 96.0%

2-methyl-1-(3-nitroquinolin-4-ylamino)propan-2-ol (129655-57-8) → 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (129655-59-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; for 4h; under 3102.97 Torr;

DOI:10.1016/j.bmcl.2009.02.100

Reference yield:

4-chloro-3-nitroquinoline (39061-97-7) → 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (129655-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / Heating

2: H₂ / Pt/C / ethyl acetate

With hydrogen; platinum on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jm049211v

Reference yield:

3-nitro-quinolin-4-ol (50332-66-6) → 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (129655-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂; DMF / CH₂Cl₂ / 3 h / Heating

2: CH₂Cl₂ / Heating

3: H₂ / Pt/C / ethyl acetate

With thionyl chloride; hydrogen; N,N-dimethyl-formamide; platinum on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jm049211v

upstream raw materials:

2-methyl-1-(3-nitroquinolin-4-ylamino)propan-2-ol

quinolin-4-ol

3-nitro-quinolin-4-ol

4-chloro-3-nitroquinoline

Downstream raw materials:

1-{2-[(benzyloxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol

Refernces

• 1、 -. "IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF". Paragraph 0013; 00106; 00111. . Retrieved 2021/10/11.
• 2、 -. "METHOD OF TREATING CANCER BY TARGETING MYELOID-DERIVED SUPPRESSOR CELLS". Page/Page column 46. . Retrieved 2017/12/29.