Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. Synthesis of tert-Butyl 3- and 4-[(2)-3-(Dimethylamino)-2-(methoxycarbonyl)prop-2-enoyl]piperidine-1-carboxylates (3a–c)
3.3. Synthesis Procedure for the Preparation of Compounds 4a, 5a, and 6a
3.3.1. tert-Butyl 4-[(2E(Z))-2-(methoxycarbonyl)-3-(2-phenylhydrazinyl)prop-2-enoyl]piperidine-1-carboxylate (4a)
3.3.2. tert-Butyl 4-[4-(methoxycarbonyl)-1-phenyl-1H-pyrazol-5-yl]piperidine-1-carboxylate (5a)
3.3.3. tert-Butyl 4-[4-(methoxycarbonyl)-1-phenyl-1H-pyrazol-3-yl]piperidine-1-carboxylate (6a)
3.4. Synthesis of tert-Butyl 4-[4-(methoxycarbonyl)-1H-pyrazol-5-yl]piperidine-1-carboxylates (5b–o)
3.4.1. tert-Butyl 4-[4-(methoxycarbonyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5b)
3.4.2. tert-Butyl 4-[4-(methoxycarbonyl)-1-(3-methylphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5c)
3.4.3. tert-Butyl 4-[1-(3-fluorophenyl)-4-(methoxycarbonyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5d)
3.4.4. tert-Butyl 4-[1-(2-fluorophenyl)-4-(methoxycarbonyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5e)
3.4.5. tert-Butyl 4-[4-(methoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5f)
3.4.6. tert-Butyl 4-[4-(methoxycarbonyl)-1-(3-methoxyphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5g)
3.4.7. tert-Butyl 4-{4-(methoxycarbonyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}piperidine-1-carboxylate (5h)
3.4.8. tert-Butyl 4-[4-(methoxycarbonyl)-1-methyl-1H-pyrazol-5-yl]piperidine-1-carboxylate (5i)
3.4.9. tert-Butyl (3R)-3-[4-(methoxycarbonyl)-1-phenyl-1H-pyrazol-5-yl]piperidine-1-carboxylate (5j)
3.4.10. tert-Butyl (3S)-3-[4-(methoxycarbonyl)-1-phenyl-1H-pyrazol-5-yl]piperidine-1-carboxylate (5k)
3.4.11. tert-Butyl (3R)-3-[4-(methoxycarbonyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5l)
3.4.12. tert-Butyl (3S)-3-[4-(methoxycarbonyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (5m)
3.4.13. tert-Butyl (3R)-3-{4-(methoxycarbonyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}piperidine-1-carboxylate (5n)
3.4.14. tert-Butyl (3S)-3-{4-(methoxycarbonyl)-1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}piperidine-1-carboxylate (5o)
3.5. Synthesis of tert-Butyl 4-[4-(methoxycarbonyl)-1H-pyrazolyl]piperidine-1-carboxylate (7)
3.6. Synthesis of tert-Butyl 4-[4-(methoxycarbonyl)-1H-pyrazolyl]piperidine-1-carboxylates (5i, 6i, 8)
3.6.1. tert-Butyl 4-[4-(methoxycarbonyl)-1-methyl-1H-pyrazol-3-yl]piperidine-1-carboxylate (6i) and tert-Butyl 4-[4-(methoxycarbonyl)-1-methyl-1H-pyrazol-5-yl]piperidine-1-carboxylate (5i)
3.6.2. tert-Butyl 4-[1-ethyl-4-(methoxycarbonyl)-1H-pyrazol-3-yl]piperidine-1-carboxylate (8)
3.7. Synthesis of 5-[1-(tert-Butoxycarbonyl)piperidinyl]-1H-pyrazole-4-carboxylic acids (9a–c)
3.7.1. 5-[1-(tert-Butoxycarbonyl)piperidin-4-yl]-1-phenyl-1H-pyrazole-4-carboxylic Acid (9a)
3.7.2. 5-[(3R)-1-(tert-Butoxycarbonyl)piperidin-3-yl]-1-phenyl-1H-pyrazole-4-carboxylic Acid (9b)
3.7.3. 5-[(3S)-1-(tert-Butoxycarbonyl)piperidin-3-yl]-1-phenyl-1H-pyrazole-4-carboxylic Acid (9c)
3.8. Synthesis of tert-Butyl 3- and 4-[4-(Phenylcarbamoyl)-1H-pyrazol-5-yl]piperidine-1-carboxylates (10a–c)
3.8.1. tert-Butyl 4-[1-phenyl-4-(phenylcarbamoyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (10a)
3.8.2. tert-Butyl (3R)-3-[1-phenyl-4-(phenylcarbamoyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (10b)
3.8.3. tert-Butyl (3S)-3-[1-phenyl-4-(phenylcarbamoyl)-1H-pyrazol-5-yl]piperidine-1-carboxylate (10c)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Entry | Solvent * | t (h) | 4a/5a/6a ** | t (h) | 4a/5a/6a ** | 5a, Yield (%) *** |
---|---|---|---|---|---|---|
1 | EtOH | 1 | 52.4/46.8/0.8 | 18 | 0/99.5/0.5 | 78 |
2 | ACN | 1 | 27.6/68.2/4.2 | 18 | 0/95.2/4.8 | 75 |
3 | CCl4 | 1 | 58.3/27.5/14.2 | 18 | 18.3/67.9/13.8 | 54 |
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Matulevičiūtė, G.; Arbačiauskienė, E.; Kleizienė, N.; Kederienė, V.; Ragaitė, G.; Dagilienė, M.; Bieliauskas, A.; Milišiūnaitė, V.; Sløk, F.A.; Šačkus, A. Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates. Molecules 2021, 26, 3808. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133808
Matulevičiūtė G, Arbačiauskienė E, Kleizienė N, Kederienė V, Ragaitė G, Dagilienė M, Bieliauskas A, Milišiūnaitė V, Sløk FA, Šačkus A. Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates. Molecules. 2021; 26(13):3808. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133808
Chicago/Turabian StyleMatulevičiūtė, Gita, Eglė Arbačiauskienė, Neringa Kleizienė, Vilija Kederienė, Greta Ragaitė, Miglė Dagilienė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Frank A. Sløk, and Algirdas Šačkus. 2021. "Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates" Molecules 26, no. 13: 3808. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133808