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[ CAS No. 88625-24-5 ]

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Chemical Structure| 88625-24-5
Chemical Structure| 88625-24-5
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CAS No. :88625-24-5 MDL No. :MFCD10697774
Formula : C5H3ClN2O Boiling Point : 211°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :142.54 g/mol Pubchem ID :21698067
Synonyms :

Safety of [ 88625-24-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 88625-24-5 ]

  • Upstream synthesis route of [ 88625-24-5 ]
  • Downstream synthetic route of [ 88625-24-5 ]

[ 88625-24-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 88625-24-5 ]
  • [ 72788-94-4 ]
Reference: [1] Patent: WO2009/134668, 2009, A2, . Location in patent: Page/Page column 29; 30
  • 2
  • [ 33332-25-1 ]
  • [ 88625-24-5 ]
YieldReaction ConditionsOperation in experiment
68% With diisobutylaluminium hydride In tetrahydrofuran; toluene at -55℃; for 1 h; Inert atmosphere Diisobutylaluminium hydride (1.0 M in toluene; 6.4 mL, 6.40 mmol) was added dropwise to a cooled solution of methyl 5-chloropyrazine-2-carboxylate (690 mg, 4.00 mmol) in THF (13.6 mL) at -55 °C. The reaction was stirred under these conditions for 1 hour and then quenched by addition of saturated aqueous NH4C1 (25 mL) and EtOAc (25 mL). An emulsion formed and 2N aqueous HC1 was added to clear the emulsion (5 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layerwas washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography, elution gradient 0 to 50percent EtOAc in heptane. Product fractions were evaporated to dryness to afford 5-chloropyrazine-2-carbaldehyde (385 mg, 68percent) as a beige solid. ‘H NMR (500 MHz, CDC13, 27 °C) 8.75 (1H, d), 8.96 (1H, d), 10.15 (1H, d).
Reference: [1] Patent: WO2018/19793, 2018, A1, . Location in patent: Page/Page column 147; 148
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354
[3] Patent: WO2012/81736, 2012, A1, . Location in patent: Page/Page column 91-92
[4] Patent: WO2018/93569, 2018, A1,
  • 3
  • [ 72788-94-4 ]
  • [ 88625-24-5 ]
YieldReaction ConditionsOperation in experiment
50.7% With manganese(IV) oxide In chloroform for 2 h; Reflux To a solution of Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite® and washed with CHCl3 (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 percent EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70percent) as a white solid.1H NMR (400 MHz, DMSO-d6) δ ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.
Reference: [1] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 196Intermediate 112B: 5-chloropyrazine-2-carbaldeh
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  • [ 36070-80-1 ]
  • [ 88625-24-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354
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