N-(2-Chloropyrimidin-4-YL)-N,2,3-trimethyl-2H-indazol-6-amine

Base Information

• Chemical Name: N-(2-Chloropyrimidin-4-YL)-N,2,3-trimethyl-2H-indazol-6-amine
• CAS No.: 444731-75-3
• Molecular Formula: C14H14ClN5
• Molecular Weight: 287.752
• Hs Code.: 2933990090
• European Community (EC) Number: 810-050-2
• UNII: GWH7RB3PB5
• DSSTox Substance ID: DTXSID70469403
• Wikidata: Q72459031
• Mol file: 444731-75-3.mol

Synonyms:444731-75-3;N-(2-CHLOROPYRIMIDIN-4-YL)-N,2,3-TRIMETHYL-2H-INDAZOL-6-AMINE;N-(2-chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-Indazol-6-amine;N-(2-CHLOROPYRIMIDIN-4-YL)-N,2,3-TRIMETHYLINDAZOL-6-AMINE;2H-Indazol-6-amine, N-(2-chloro-4-pyrimidinyl)-N,2,3-trimethyl-;N-(2-Chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazol-6-amine;DVGMRZQSSNNTFY-UHFFFAOYSA-N;GWH7RB3PB5;SCHEMBL589205;DTXSID70469403;BCP13045;CS-B0769;MFCD12923006;AKOS015918031;CCG-358824;SB18242;AC-25865;AS-71135;A7064;AM20090657;FT-0687641;EN300-265810;F11991;J-522901;F9995-1141;(2-Chloro-pyrimidin-4-yl)-(2,3-dimethyl-2H-indazol-6-yl)-methyl-amine;6-[N-(2-chloro-4-pyrimidinyl)methylamino]-2,3-dimethyl-2H-indazole;N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2h-indazole-6-amine

Chemical Property of N-(2-Chloropyrimidin-4-YL)-N,2,3-trimethyl-2H-indazol-6-amine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 167-173℃
• Refractive Index: 1.673
• Boiling Point: 524.447 °C at 760 mmHg
• PKA: 2.82±0.30(Predicted)
• Flash Point: 270.976 °C
• PSA: 46.84000
• Density: 1.339 g/cm³
• LogP: 3.09300
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 287.0937732
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC(=CC2=NN1C)N(C)C3=NC(=NC=C3)Cl
• Uses: N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amine is an impurity of Pazopanib (P210925), an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

Technology Process of N-(2-Chloropyrimidin-4-YL)-N,2,3-trimethyl-2H-indazol-6-amine

There total 20 articles about N-(2-Chloropyrimidin-4-YL)-N,2,3-trimethyl-2H-indazol-6-amine 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: 97.0%

2,6-Dichloropyrimidine (3934-20-1) + N,2,3-trimethyl-2H-indazole-6-amine (1376676-65-1) → N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine (444731-75-3)

Guidance literature:

With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 85 ℃; for 3h;

Reference yield: 90.4%

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine (444731-74-2) + methyl iodide (74-88-4) → N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine (444731-75-3)

Guidance literature:

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine; With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20 - 25 ℃; for 0.166667h;

methyl iodide; In DMF (N,N-dimethyl-formamide); at 20 - 30 ℃; for 1 - 2h;

Reference yield: 90.4%

methyl iodide (74-88-4) → N-(2-chloropyrimidin-4-yl)-N-methyl-2,3-dimethyl-2H-indazole-6-amine (444731-75-3)

Guidance literature:

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine; With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 25 ℃; for 0.166667h;

methyl iodide; In N,N-dimethyl-formamide; at 20 - 30 ℃; for 0.166667h;

With water; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 1.16667h; Product distribution / selectivity;

upstream raw materials:

methyl iodide

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine

carbonic acid dimethyl ester

N-(2-chloro-4-pyrimidinyl)-N-(3-methyl-1H-indazol-6-yl)amine

Downstream raw materials:

5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide methanesulfonic acid salt

5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)-N-methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide hydrochloride

Refernces

• 1、 -. "Preparation method of pazopanib intermediate". Paragraph 0181-0184. . Retrieved 2021/03/24.
• 2、 -. "Green preparation method of palatinib hydrochloride (by machine translation)". Paragraph 0086-0094. . Retrieved 2019/08/01.