ChemicalBook CAS DataBase List LDN-193189

LDN-193189 synthesis

8synthesis methods

Product Name:LDN-193189
CAS Number:1062368-24-4
Molecular formula:C25H22N6
Molecular Weight:406.48

1-Piperazinecarboxylic acid, 4-[4-[3-(4-quinolinyl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]-, phenylmethyl ester

1062368-23-3

1062368-24-4

The general procedure for the synthesis of 4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinolines, using the compound (CAS: 1062368-23-3) as starting material, was as follows: 5% Pd/C catalyst and intermediate 12 (20 mg, 0.37 mmol) were dissolved in a mixture of methanol (3 mL) and dichloromethane (2 mL) solvent for degassing. Subsequently, the reaction was carried out under hydrogen atmosphere for 4 hours at room temperature. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to afford the target product 13 (13 mg, 86% yield). The product was characterized by 1H NMR (DMSO-d6) with the following chemical shifts: δ 9.75 (d, J = 2.2 Hz, 1H), 9.40 (br.s, 1H), 9.29 (d, J = 5.9 Hz, 1H), 9.28 (d, J = 2.2 Hz, 1H), 9.07 (s, 1H), 8.70 (d, J = 8.4 Hz, 1H), 8.70 (d, J = 8.4 Hz, 1H), and 8.51 (d, J = 5.9 Hz, 1H), 8.47 (d, J = 8.4 Hz, 1H), 8.21 (t, J = 7.6 Hz, 1H), 7.99 (t, J = 7.6 Hz, 1H), 7.88 (d, J = 8.8 Hz, 2H), 7.19 (d, J = 8.8 Hz, 2H), 3.51-3.58 (m, 4H). 3.20-3.30 (m, 4H).

4363-93-3 Synthesis

4363-93-3
234 suppliers
$7.00/250mg

1062368-24-4
178 suppliers
$35.00/1mg

Yield:-

Steps:

Multi-step reaction with 8 steps
1.1: methanol; sodium tetrahydroborate / 1.33 h / 0 - 20 °C
2.1: thionyl chloride / dichloromethane / 2.33 h / 0 - 20 °C
2.2: pH > 7 / Saturated solution
3.1: N,N-dimethyl-formamide / 20 - 80 °C
4.1: 6 h / 120 °C
5.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C
5.2: Saturated solution
6.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation
7.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere
8.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr

References:

THE GENERAL HOSPITAL CORPORATION;THE BRIGHAM AND WOMEN'S HOSPITAL, INC. WO2009/114180, 2009, A1