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[ CAS No. 35445-32-0 ]

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2D
Chemical Structure| 35445-32-0
Chemical Structure| 35445-32-0
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Product Details of [ 35445-32-0 ]

CAS No. :35445-32-0MDL No. :MFCD08703647
Formula : C8H12N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :168.19Pubchem ID :12685481
Synonyms :

Computed Properties of [ 35445-32-0 ]

TPSA : 44.1 H-Bond Acceptor Count : 3
XLogP3 : 1 H-Bond Donor Count : 0
SP3 : 0.50 Rotatable Bond Count : 3

Safety of [ 35445-32-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35445-32-0 ]

  • Upstream synthesis route of [ 35445-32-0 ]
  • Downstream synthetic route of [ 35445-32-0 ]

[ 35445-32-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 51605-32-4 ]
  • [ 74-88-4 ]
  • [ 35445-32-0 ]
YieldReaction ConditionsOperation in experiment
35% With potassium carbonate In acetonitrileReflux Ethyl 4-methyl-1 H-imidazole-5-carboxylate (463 mg, 3.00 mmol, 1 eq) was combined with iodomethane (0.19 mL, 3.00 mmol, 1 eq) and potassium carbonate (828 mg, 6.00 mmol, 2 eq) in acetonitrile and stirred overnight at reflux. The reaction mixture was cooled to ambient temperature, inorganics filtered off, and the filtrate concentrated to dryness. The residue was purified on an 80 g silica gel cartridge eluted with 100percent EtOAc to 10percent CH3OH/DCM to give the two regioisomeric products. The first eluting isomer was identified as the title compound (185 mg, 1.95 mmol, 35percent) by comparative NOESY and HMBC NMR. 1 H NMR (400 MHz, DMSO- d6) δ ppm 7.74 (s, 1 H), 4.25 (q, J=7.14 Hz, 2 H), 3.76 (s, 3 H), 2.34 (s, 3 H), 1.30 (t, J=7.10 Hz, 3 H). LC-MS (ES+) m/z 169.08 [M+H]
31% With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 90℃; for 120 h; ETHEI 1 4-DIMETHVL-1H-IMIDAZOLE-5-CARBOXYLATE] To a solution of the [AVAILABLE ETHYL 4-METHYL-1 H-IMIDAZOLE-5-CARBOXYLATE] (5.0 [G,] 32.5 [MMOL)] in DMF (50 mL) was added [NAHC03] (5.72 g, 2. [1EQ.)] and methyl iodide (2.43 [ML, 1.2 EQ. ). THE REACTION WAS STIRRED AT 90XB0;C DURING 5 DAYS. AFTER EVAPORATION OF THE] solvant, the residue was diluted in DCM and washed with water. The organic layer was dried over [NA2SO4] and evaporated off. After purification by flash chromatography using DCM as eluent, the title compound was obtained as a yellow oil (1.69 g, 0.01 mol) in [31percent] yield;'H NMR (CDCI3, 300 MHz) [6] 7.86 (s, 1H), 4.36 (q, 2H), 3.89 (s, 3H), 2.47 (s, 3H), 1.4 (t, 3H)
Reference: [1] Patent: WO2008/157273, 2008, A1, . Location in patent: Page/Page column 86
[2] Patent: WO2004/6922, 2004, A1, . Location in patent: Page/Page column 56
[3] Patent: US2004/122018, 2004, A1, . Location in patent: Page 465
  • 2
  • [ 67-56-1 ]
  • [ 51605-32-4 ]
  • [ 35445-32-0 ]
YieldReaction ConditionsOperation in experiment
59.8% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere To a mixture of ethyl 4-methyl-1H-imidazole-5-carboxylate (7.30 g, 45.9 mmol) in THF (60 mL) is added MeOH (2.23 mL, 55.1 mmol) and triphenylphosphine (14.8 g, 55.1 mmol). The reaction is cooled to 0° C. under N2 and diethyl azodicarboxylate (9.0 mL, 17.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred overnight. The volatiles are evaporated in vacuo. Ether (50 mL) is added. The mixture is stirred at room temperature for 30 minutes, filtered, the filter cake is washed with ether (50 mL). The filtrate and ether washings are combined and are sequentially washed with water (30 mL) and brine (30 mL). The organic phase is dried over Na2SO4, evaporated in vacuo to provide the crude product. The crude product is subjected to silica gel flash column eluting with 30percent EtOAc in hexanes to EtOAc to give the title compound (5.13 g, 59.8percent) as a yellow oil. LC/MS (m/z): 169 (M+H).
Reference: [1] Patent: US2018/194755, 2018, A1, . Location in patent: Paragraph 0069-0070
  • 3
  • [ 51605-32-4 ]
  • [ 74-88-4 ]
  • [ 35445-32-0 ]
  • [ 74531-82-1 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 1, p. 144 - 147
  • 4
  • [ 51605-32-4 ]
  • [ 74-88-4 ]
  • [ 35445-32-0 ]
  • [ 74531-82-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 7, p. 1463 - 1473
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