[ CAS No. 69879-22-7 ]

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2D
Chemical Structure| 69879-22-7
Chemical Structure| 69879-22-7
Structure of 69879-22-7

Quality Control of [ 69879-22-7 ]

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Related Doc. of [ 69879-22-7 ]

SDS

Product Details of [ 69879-22-7 ]

CAS No. :69879-22-7MDL No. :MFCD09757481
Formula :C6H6N2OBoiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :122.12Pubchem ID :18404634
Synonyms :

Computed Properties of [ 69879-22-7 ]

TPSA : 56 H-Bond Acceptor Count : 3
XLogP3 : 0 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 69879-22-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305 P351 P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 69879-22-7 ]

  • Upstream synthesis route of [ 69879-22-7 ]

[ 69879-22-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 4214-73-7 ]
  • [ 69879-22-7 ]
YieldReaction ConditionsOperation in experiment
73.16% With lithium aluminium tetrahydride In tetrahydrofuran for 1.50 h; To a solution of compound 53.9 (10 g, 83.95 mmol, 1 eq) in THF (150 mL) wasadded LAH (6.37 g, 167.90 mmol, 2 eq) at 0°C. The mixture was stirred at 0°C for 1.5 hours.The reaction mixture was quenched by addition saturated sodium sulfate at 0 °C and added100 ml H20 then extracted with ethyl acetate (100 mL x 3). The combined organic layerswere washed with saturated brines (30 mL x 1), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure to give the product compound 53.8 (7.50 g, 61.42mmol, 73.16percent yield) as a yellow oil. LCMS (ESI): m/z: [M + H] called for C6H6N20: 123;found 123; RT=0.099 mm.
30% With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; 4.1.1
Synthesis of 6-aminopyridine-3-carboxaldehyde
A 1M solution of diisobutylaluminum hydride (DIBAL) in hexane (10 mL) was added to a solution of 6-amino-5-cyanopyridine (10 mmol) in dry THF (50 mL) cooled at 0 °C.
The ice-bath was removed, and additional 7.1 mL of a 1M solution of DIBAL in hexane were added in two successive portions.
After stirring for additional 30 min, the reaction was quenched by the dropwise addition of dry MeOH (15 mL).
The mixture was partitioned between 100 mL of AcOEt and 70 mL of 2N HCl.
The aqueous layer was treated with 75 mL of 2N NaOH and extracted with AcOEt.
The organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to dryness.
The residue was purified by column chromatography on silica gel eluting with CHCl3/AcOEt 1:4. Yield: 30percent, mp = 174-175 °C. IR (KBr): 3366, 3121, 1659 cm-1. 1H NMR (CD3OD, 400 MHz): δ (ppm) 9.67 (s, 1H, CHO), 8.41 (d, 1H, H2, J2-4 = 1.6 Hz), 7.87 (dd, 1H, H4, J4-5 = 8.8 Hz, J2-4 = 1.6 Hz), 6.63 (d, 1H, H5, J4-5 = 8.8 Hz), 3.31 (s, 2H, NH2).
13C NMR (CDCl3, 100 MHz): δ (ppm) 191.15, 164.46, 155.78, 137.39, 123.92, 109.99.
Reference: [1] Patent: WO2018/209132, 2018, A1. Location in patent: Paragraph 0458; 0489
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 292 - 300
[3] Patent: US2009/143420, 2009, A1. Location in patent: Page/Page column 7
[4] Patent: EP1724263, 2006, A1. Location in patent: Page/Page column 55
[5] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0177; 0178
  • 2
  • [ 22790-82-5 ]
  • [ 69879-22-7 ]
Reference: [1] Doklady Akademii Nauk SSSR, 1949, vol. 65, p. 843[2] Chem.Abstr., <1949> 6626,
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