N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea

Base Information

• Chemical Name: N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea
• CAS No.: 1020172-07-9
• Molecular Formula: C30H28FN7O3
• Molecular Weight: 553.596
• Mol file: 1020172-07-9.mol

Synonyms:N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea;4-[3-Fluoro-4-({[3-(2-methyl-2-propanyl)-1-(6-quinolinyl)-1H-pyrazol-5-yl]carbamoyl}amino)phenoxy]-N-methyl-2-pyridinecarboxamide;

Chemical Property of N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea

Chemical Property:

• Boiling Point: 666.8±55.0 °C at 760 mmHg
• PKA: 12.25±0.70(Predicted)
• Flash Point: 357.0±31.5 °C
• PSA: 126.55000
• Density: 1.3±0.1 g/cm³
• LogP: 6.52550
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rebastinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Rebastinib is an orally bioavailable tyrosine kinase inhibitor that inhibits Abl1 (IC50 = 0.8 nM) as well as the gatekeeper mutant Abl1T315I (IC50 = 4 nM) and the activation loop mutant Abl1H396P. It also inhibits the Src family kinases Src, Lyn, Fgr, and Hck and the tyrosine kinases KDR, FLT3, and Tie2 at nanomolar concentrations. Rebastinib inhibits mutant Abl1T315I signaling and prolongs survival in a mouse Ba/F3 cell allograft model. Rebastinib also exhibits in vivo antineoplastic activity against cells with the T674I point mutation of FIP1-like-1-platelet-derived growth factor receptor α.
• Uses: A conformational control inhibitor of Abl1 and Abl1-T315I with IC50s of 0.8 nM and 4 nM, respectively. Rebastinib shows the selectivity for growth inhibition of Bcr-Abl-positive cells by its marked inhibition of CML cell lines compared to non-CML leukemia lines. Rebastinib (DCC-2036) is a conformational control Bcr-Abl inhibitor for Abl1(WT) and Abl1(T315I) with IC50 of 0.8 nM and 4 nM, also inhibits SRC, LYN, FGR, HCK, KDR, FLT3, and Tie-2, and low activity to seen towards c-Kit. Phase 1. It is a COVID19-related research product.

Technology Process of N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea

There total 10 articles about N-[3-tert-Butyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl]-N'-[2-fluoro-4-[(2-(methylcarbamoyl)pyridin-4-yl)oxy]phenyl]urea 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: 46.0%

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide (757251-39-1) + 2,2,2-trichloroethyl (3-(tert-butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)carbamate (1011464-72-4) → DCC-2036 (1020172-07-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70 ℃; for 8h;

Reference yield:

6-hydroxyquinoline (580-16-5) → DCC-2036 (1020172-07-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / dichloromethane / 4 h / 20 °C

2: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate / toluene / 16 h / 90 °C / Inert atmosphere

3: hydrogenchloride / ethanol / Reflux

4: dmap; pyridine / dichloromethane / 1.33 h / -10 °C

5: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 8 h / 70 °C

With pyridine; hydrogenchloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; dimethyl sulfoxide; toluene;

Reference yield:

5-tert-butyl-2-quinolin-6-yl-2H-pyrazol-3-ylamine (897373-62-5) → DCC-2036 (1020172-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; pyridine / dichloromethane / 1.33 h / -10 °C

2: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 8 h / 70 °C

With pyridine; dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

2,2,2-trichloroethyl (3-(tert-butyl)-1-(quinolin-6-yl)-1H-pyrazol-5-yl)carbamate

6-hydroxyquinoline

quinolin-6-yl triflate

Refernces

• 1、 -. "METHODS AND COMPOSITIONS FOR THE TREATMENT OF MYELOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES". Paragraph 00358. . Retrieved 2013/03/26.