ChemicalBook CAS DataBase List 1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE

1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE synthesis

4synthesis methods

Product Name:1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE
CAS Number:315203-39-5
Molecular formula:C19H20Cl2N4
Molecular Weight:375.29

1-[(2,6-dichlorophenyl)methyl]-6-nitro-3-(pyrrolidin-1-ylmethyl)indazole

372963-38-7
0 suppliers
inquiry

1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE

315203-39-5
32 suppliers
$24.00/100mg

Yield:315203-39-5 69%

Reaction Conditions:

with iron(III) chloride hexahydrate;pyrographite;hydrazine hydrate in methanol at 100; for 2 h;Sealed tube;

Steps:

4.7 4.4.7. 1-(2,6-Dichlorobenzyl)-3-(pyrrolidin-1-ylmethyl)-1H-indazol-6-amine (9)

To an oven dried pressure tube with stir bar was added indazole8 (18 mg, 0.044 mmol) and MeOH (5 mL). FeCl36H2O (25 mol%,2.6 mg), hydrazine monohydrate solution (65% active hydrazine,0.05 mL, 0.7 mmol), and activated charcoal (20 mg) were added,the tube was capped tightly, and the reaction was stirred at 100C for 2 h. A sample aliquot was taken from the reaction, concentratedunder reduced pressure, dissolved in a minimal amount ofHPLC grade MeCN, and analyzed with LCMS to confirm reactioncompletion. The reaction was filtered, the charcoal and filteredsolids were washed with MeOH (10 mL), and the filtrate was concentratedunder reduced pressure to give crude material that wasdry loaded using silica onto a 5 g silica column and purified withflash chromatography (0-20% MeOH/DCM) to give 9 (11.5 mg) asa white solid in 69% yield. LC-MS tR = 1.44 min (CharacterizationMethod A); m/z = 374.95 (M+H+); 1H NMR (300 MHz, CDCl3) d =7.57 (d, J = 8.5 Hz, 1H), 7.37 (d, J = 8.2 Hz, 2H), 7.31-7.20 (s, 1H),6.63 (d, J = 8.8 Hz, 1H), 6.58 (s, 1H), 5.63 (s, 2H), 4.29 (s, 2H), 3.96(br. s., 2H), 3.13 (br. s., 4H), 1.84 (br. s., 4H); 13C NMR (75 MHz,CDCl3) d = 146.5, 142.5, 137.0, 131.6, 130.3, 128.8, 121.0, 117.7,113.7, 92.2, 52.3, 48.5, 48.2, 23.9.

References:

Gandhi, Disha M.;Majewski, Mark W.;Rosas, Ricardo;Kentala, Kaitlin;Foster, Trevor J.;Greve, Eric;Dockendorff, Chris [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 9,p. 2514 - 2529]

4769-96-4
264 suppliers
$9.00/250mg

315203-39-5
32 suppliers
$24.00/100mg

References

315203-37-3 Synthesis

315203-37-3
87 suppliers
$45.00/1mg

315203-39-5
32 suppliers
$24.00/100mg

References

1H-Indazole, 6-nitro-3-(1-pyrrolidinylmethyl)-

315203-38-4
0 suppliers
inquiry

315203-39-5
32 suppliers
$24.00/100mg

References

1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE Related Search:

1-METHYL-1H-INDAZOL-6-YLAMINE