1-(2,6-DICHLORO-BENZYL)-3-PYRROLIDIN-1-YLMETHYL-1H-INDAZOL-6-YLAMINE synthesis
- 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](/CAS/20180529/GIF/372963-38-7.gif)
372963-38-7
315203-39-5
To an oven-dried pressure tube equipped with a stirrer was added 1-(2,6-dichlorobenzyl)-1H-indazol-6-amine (18 mg, 0.044 mmol) and methanol (5 mL). Subsequently, ferric chloride hexahydrate (25 mol%, 2.6 mg), 65% hydrazine monohydrate solution (0.05 mL, 0.7 mmol) and activated charcoal (20 mg) were added, the reaction tube was sealed, and the reaction was stirred for 2 hours at 100 °C. During the reaction, a small amount of the reaction solution was taken, concentrated under reduced pressure and dissolved in a minimal amount of high-performance liquid chromatography-grade acetonitrile for LC-MS analysis to monitor the progress of the reaction. After completion of the reaction, the reaction mixture was filtered, the activated carbon and filter cake were washed with methanol (10 mL), the filtrates were combined and concentrated under reduced pressure to obtain the crude product. The crude product was mixed with silica gel and dried, then up-sampled onto a 5 g silica gel column and purified by fast column chromatography (0-20% methanol/dichloromethane gradient elution) to afford the target compound, 1-(2,6-dichlorobenzyl)-3-(pyrrolidin-1-ylmethyl)-1H-indazol-6-amine (11.5 mg, 69% yield), as a white solid. lC-MS retention time tR = 1.44 min (Method A); mass spectrum m/z = 374.95 ([M+H]+); 1H NMR (300 MHz, CDCl3) δ = 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), and 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) δ = 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.
372963-38-7
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315203-39-5
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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
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315203-39-5
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$24.00/100mg
315203-37-3
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315203-39-5
32 suppliers
$24.00/100mg
315203-38-4
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315203-39-5
32 suppliers
$24.00/100mg