In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 527681-61-4, name is 3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde, the common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9NO2
suspension of (1 /?)-1-[(4-amino-1-piperidinyl)methyl]-6-methyl-1 ,2-dihydro- 4H,9H-imidazo[1 ,2,3-ij]-1 ,8-naphthyridine-4,9-dione dihydrochloride (50mg, 0.135 mmol) in chloroform (4 ml) and methanol (0.200 ml) at room temperature under nitrogen was treated with triethylamine (0.057 ml, 0.406 mmol) and stirred for 0.25h (the suspension turned into a solution). 3,4-Dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, example 5(c)) (22.06 mg, 0.135 mmol) was then added and the reaction was stirred at room temperature for 0.5h.Sodium triacetoxyborohydride (90 mg, 0.406 mmol) was then added and the reaction was stirred at room temperature. After 2h there was still some starting material so 30 mg of sodium triacetoxyborohydride were added. After 1 h sat NaHCO3 (25ml_) was added followed by 20% MeOH/DCM (25ml_) and the aqueous was extracted and then separated from the organic layer. The aqueous was extracted again twice with 20%MeOH/DCM (2x25ml_). Combined organics were dried NaSO4, filtered and evaporated to afford the crude. The crude was purified by silica chromatography (0- 20%MeOH/DCM) to afford 41 mg of desired compound (65.7%) as a pale yellow gum. 1H NMR deltaH CDCI3, (400MHz) 1.30-1.45 (m, 2H), 1.80-1.89 (m, 2H), 1.99-2.05 (m, 2H), 2.15-2.4 (m, 5H), 2.45-2.58 (m, 1 H), 2.62-2.67 (m, 2H), 2.74-2.78 (m, 2H), 2.96 (d, 1 H), 3.05-3.09 (m, 1 H), 3.79 (s, 2H), 4.19-4.22 (m, 2H), 4.28-4.33 (m, 1 H), 4.51-4.55 (m, 1 H), 4.95-5.05 (m, 1 H), 6.15 (s, 1 H), 6.26 (d, 1 H), 6.97 (s, 1 H), 7.56 (d, 1 H), 8.07 (s, 1 H). MS (ES+) m/z 462 (MH+).The compound was dissolved in a small amount of MeOH/DCM and treated with 1eq of a 1 M solution of HCI in diethyl ether. The solvents were removed and the solid was dried in the desiccator (in the presence of P2O5) overnight to afford the mono-HCI salt of the product as a yellow solid (45.9mg, 64.8%). LCMS was consistent with product
The synthetic route of 527681-61-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXO GROUP LIMITED; GIORDANO, Ilaria; HENNESSY, Alan, Joseph; WO2010/43714; (2010); A1;,
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