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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
1429505-54-3

[4-(4-FLUORO-BENZYL)-4-HYDROXY-PIPERIDIN-1-YL]-(2-PYRIMIDIN-4-YL-PYRIDIN-3-YL)-METHANONE synthesis

4synthesis methods
1429505-77-0 Synthesis
4-(4-FLUOROBENZYL)-4-HYDROXYPIPERIDINE HCL

1429505-77-0
13 suppliers
$285.00/100mg

2-PYRIMIDIN-4-YL-NICOTINIC ACID

1429555-05-4
10 suppliers
$351.00/1g

[4-(4-FLUORO-BENZYL)-4-HYDROXY-PIPERIDIN-1-YL]-(2-PYRIMIDIN-4-YL-PYRIDIN-3-YL)-METHANONE

1429505-54-3
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Yield:1429505-54-3 100%

Reaction Conditions:

Stage #1: 2-(pyrimidin-4-yl)nicotinic acidwith N-ethyl-N,N-diisopropylamine;O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate in N,N-dimethyl-formamide at 0; for 0.333333 h;
Stage #2: 4-(4-fluorobenzyl)piperidin-4-ol hydrochloride in N,N-dimethyl-formamide at 25; for 0.5 h;

Steps:

3.3 Step 3

To a solution of 2-(pyrimidin-4-yl)nicotinic acid (200 mg, 0.994 mmol) in DMF (10 mL) was added HATU (566 mg, 1.49 mmol) at 0oC. To this mixture was added DIPEA (385 mg, 2.98 mmol) dropwise. After stirring at 0oC for 20 minutes, 4-[(4-fluorophenyl)methyl]piperidin-4-ol hydrochloride (244 mg, 0.99 mmol) was added. The reaction was warmed to 25oC and stirred for 30 minutes. The reaction mixture was concentrated. A second reaction was performed in parallel and the crude reaction mixtures were combined for purification. The combined reactions were purified by prep-HPLC (column: Xamide 150*30mm 5μm, gradient: 15-45% B (A= water, 10mM NH4HCO3, B= ACN), flow rate: 25 mL/min) to give (4-(4-fluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(pyrimidin-4-yl)pyridin-3-yl)methanone (325 mg, 100%).1H-NMR (400 MHz, CDCl3) δH 9.19 (s, 0.5H), 8.94 (s, 0.5H), 8.90-8.81 (m, 1H), 8.76-8.72 (m, 1H), 8.29-8.18 (m, 1H), 7.75-7.60 (m, 1H), 7.52-7.38 (m, 1H), 7.18-7.12 (m, 2H), 7.05-6.98 (m, 2H), 4.70-4.46 (m, 1H), 3.64-2.88 (m, 4H), 2.77 (s, 2H), 1.95-1.61 (m, 2H), 1.41-1.24 (m, 1H), 1.21 (s, 1H). LC-ELSD/MS purity 100%, ESI cal. for C22H22FN4O2[M +H]+393, found 393.

References:

WO2022/115620,2022,A1 Location in patent:Paragraph 0271; 0276-0277

4763-58-0 Synthesis
2-ACETYL-NICOTINIC ACID ETHYL ESTER

4763-58-0
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[4-(4-FLUORO-BENZYL)-4-HYDROXY-PIPERIDIN-1-YL]-(2-PYRIMIDIN-4-YL-PYRIDIN-3-YL)-METHANONE

1429505-54-3
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References
3-Pyridinecarboxylic acid, 2-(1-ethoxyethenyl)-, ethyl ester

1429505-88-3
0 suppliers
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[4-(4-FLUORO-BENZYL)-4-HYDROXY-PIPERIDIN-1-YL]-(2-PYRIMIDIN-4-YL-PYRIDIN-3-YL)-METHANONE

1429505-54-3
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References
1256794-15-6 Synthesis
2-PYRIMIDIN-4-YL-NICOTINIC ACID ETHYL ESTER

1256794-15-6
9 suppliers
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[4-(4-FLUORO-BENZYL)-4-HYDROXY-PIPERIDIN-1-YL]-(2-PYRIMIDIN-4-YL-PYRIDIN-3-YL)-METHANONE

1429505-54-3
6 suppliers
inquiry

References