Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI)
- Product Name
- Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI)
- CAS No.
- 323578-37-6
- Chemical Name
- Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI)
- Synonyms
- Ritlecitinib Impurity 2;6-methylpyridin-3-ylcarbamate;tert-Butyl (6-methylpyridin-3-yl);tert-butyl 6-methylpyridin-3-ylcarbamate;Tert butyl 6- methyl pyridine -3- carbamate;tert-butyl N-(6-methylpyridin-3-yl)carbamate;Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-;(6-Methyl-pyridin-3-yl)-carbaMic acid tert-butyl ester;(6-Methyl-3-Pyridinyl)-Carbamic Acid 1,1-Dimethylethyl Ester;Carbamic acid, N-(6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester
- CBNumber
- CB31052025
- Molecular Formula
- C11H16N2O2
- Formula Weight
- 208.26
- MOL File
- 323578-37-6.mol
Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI) Property
- Melting point:
- 114-115 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
- Boiling point:
- 262.7±28.0 °C(Predicted)
- Density
- 1.108±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 12.94±0.70(Predicted)
- Appearance
- White to off-white Solid
N-Bromosuccinimide Price
- Product number
- B429130
- Product name
- tert-butyl6-methylpyridin-3-ylcarbamate
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- KMA0199
- Product name
- 5-(Boc-Amino)picoline
- Packaging
- 1g
- Price
- $319
- Updated
- 2021/12/16
- Product number
- 189628
- Product name
- tert-Butyl 6-methylpyridin-3-ylcarbamate
- Packaging
- 1g
- Price
- $366
- Updated
- 2021/12/16
- Product number
- CHM0394246
- Product name
- TERT-BUTYL-(6-METHYLPYRIDIN-3-YL)CARBAMATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $495.29
- Updated
- 2021/12/16
- Product number
- 189628
- Product name
- tert-Butyl 6-methylpyridin-3-ylcarbamate
- Packaging
- 5g
- Price
- $1096
- Updated
- 2021/12/16
Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI) Chemical Properties,Usage,Production
Synthesis
80287-53-2
24424-99-5
323578-37-6
Step 1. Synthesis of tert-butyl (6-methylpyridin-3-yl)carbamate. Di-tert-butyl dicarbonate (55.5 g, 298 mmol) was slowly added dropwise to a solution of 6-methylpyridin-3-amine (25 g, 231 mmol) in ethanol (100 mL) at 0 °C. After the dropwise addition, the reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by TLC (unfolding agent: petroleum ether/ethyl acetate, 2:1) to confirm complete consumption of 6-methylpyridin-3-amine. Upon completion of the reaction, the reaction mixture was filtered and the filter cake was washed with ethanol (30 mL x 3). The filtrates were combined and concentrated under reduced pressure to give a yellow residue. This residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate, 4:1 to 1:1) to afford tert-butyl (6-methylpyridin-3-yl)carbamate (32.5 g, 67.4% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 8.30 (d, J = 2.0 Hz, 1H), 7.86 (br s, 1H) 7.10 (d, J = 8.5 Hz, 1H), 6.57 (br s, 1H), 2.49 (s, 3H), 1.51 (s, 9H). Step 2. Synthesis of racemic-cis/trans-tert-butyl (6-methylpiperidin-3-yl)carbamate. Platinum oxide (2.5 g) was added to a dry hydrogenation flask under argon protection. Then a solution of tert-butyl (6-methylpyridin-3-yl)carbamate (33 g, 158.5 mmol) in acetic acid (300 mL) was added, and the resulting mixture was hydrogenated at 50 °C under 55 psi hydrogen pressure for 30 hours. The progress of the reaction was monitored by TLC (unfolding agent: petroleum ether/ethyl acetate, 2:1) to confirm complete consumption of the starting material. Upon completion of the reaction, the reaction mixture was filtered and the filter cake was washed with methanol (50 mL x 2). The filtrates were combined and evaporated under reduced pressure to afford tert-butyl (6-methylpiperidin-3-yl)carbamate (34 g, 100% yield) as a yellow oil (cis/trans ratio 2:1), which was used directly in the next step of the reaction without further purification.LC/MS (M + H) 215.2.
References
[1] Patent: US2015/158864, 2015, A1. Location in patent: Paragraph 0270
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1971 - 1993
[3] Patent: WO2012/148775, 2012, A1. Location in patent: Page/Page column 113; 114
[4] Patent: WO2010/16005, 2010, A1. Location in patent: Page/Page column 135-136
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5580 - 5590
Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI) Preparation Products And Raw materials
Raw materials
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View Lastest Price from Carbamic acid, (6-methyl-3-pyridinyl)-, 1,1-dimethylethyl ester (9CI) manufacturers
- Product
- tert-butyl 6-methylpyridin-3-ylcarbamate 323578-37-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-27
- Product
- tert-Butyl (6-methylpyridin-3-yl)carbamate 323578-37-6
- Price
- US $0.00/g
- Min. Order
- 5g
- Purity
- >95.00%
- Supply Ability
- 5g
- Release date
- 2024-04-01
- Product
- tert-butylN-(6-methylpyridin-3-yl)carbamate 323578-37-6
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99.5%
- Supply Ability
- 100 tons
- Release date
- 2022-01-14