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Chemical Structure| 1201935-35-4 Chemical Structure| 1201935-35-4

Structure of 1201935-35-4

Chemical Structure| 1201935-35-4

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Product Details of [ 1201935-35-4 ]

CAS No. :1201935-35-4
Formula : C9H14N4O2
M.W : 210.23
SMILES Code : CN1CCC(N2C=C([N+]([O-])=O)C=N2)CC1

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Application In Synthesis of [ 1201935-35-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1201935-35-4 ]

[ 1201935-35-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1201935-35-4 ]
  • [ 1201935-36-5 ]
YieldReaction ConditionsOperation in experiment
98% With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 16 h; Under hydrogen (1 atm), to a solution of compound 64-b (500 mg, 2.38 mmol) in ethanol (10 mL) was added 10percent Pd—C (0.1 g). The mixture was stirred at 25° C. for 16 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give red brown oil 64-a (420 mg, yield: 98percent), which was used directly for the next step without purification. LC-MS (ESI): m/z=181 [M+H]+.
80% With 40% Pd/C; hydrogen In ethanol A par flask was charged with 1 -methyl-4-(4-nitro- 1 H-pyrazol- 1 -yl)piperidine14 (16.0 g, 41.0 mmol) and ethanol (400 mL) followed by addition of Pd-C (40percent w/w,6.40 g). The flask was evacuated under vacuum and then purged with hydrogen. The reaction was stirred under hydrogen atmosphere (30 psi). The reaction was monitored by TLC. It was then filtered through sintered funnel with a pad of celite, washed with methanol and concentrated under reduced pressure to afford precursor-03 as a pink solid (11.0 g, 80percent yield) that was taken as such for the next step without any further purification. ‘H NMR (400 MHz, DMSO-d6): 6 7.04 (s, 111), 6.89 (s, 1H), 3.83-3.89 (m, 3H), 2.79-2.82 (m, 211), 2.01 (s, 311), 1.90-2.01 (m, 2H), 1.75-1.86 (m, 4H). Similarly, tert-butyl 4-(4-amino- 1 H-pyrazol- 1 -yl)piperidine- 1 -carboxylate (Precursor-04) was prepared from 13 using the nitro group reduction condition described above. MS: 167.10(M+H).
79% With hydrogen In ethanol at 25℃; for 16 h; Inert atmosphere b) A mixture of l-methyl-4-(4-nitro-lH-pyrazol-l-yl)piperidine (24.05 g, 114.40 mmol) and 5percent palladium on carbon (5 g, 2.4 mmol) in EtOH (240 mL) was stirred under an atmosphere of hydrogen (1 atm) at 25°C for 16 hours. The mixture was filtered and the filtrate evaporated to leave l-(l-methylpiperidin-4- yl)pyrazol-4-amine (16.39 g, 79percent yield); 1H NMR spectrum (300 MHz, DMSO): δ 1.93 - 2.03 (3H, m), 2.10 - 2.16 (4H, m), 2.33 (3H, s), 2.79 (IH, br s), 2.94 - 2.97 (2H, m), 3.97 - 4.05 (IH, m), 7.06 (IH, s), 7.14 (IH, s); Mass spectrum: m/z (ESI+) (M+H)+ = 181.29.
References: [1] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0401; 0403.
[2] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 00075.
[3] Patent: WO2009/153589, 2009, A1, . Location in patent: Page/Page column 109.
[4] Patent: US2010/317680, 2010, A1, .
[5] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0339-0340.
 

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