Synthetic Route of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A mixture of 9-(2-methyloxazol- 4-yl)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoline-2,5-dione (140 mg, 0.45 mmol) in DCE (10 mL) was treated with POCI3 (84 mu, 0.91 mmol) and heated to 100 °C for 1 h. The mixture was then allowed to cool to RT, poured onto cold H20 and extracted with DCM. The org. phases were dried over Na2SO,, filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (5 mL) and 4-cyclopropyl-1H-imidazole (59 mg, 0.54 mmol) and pyridine (110 mu, 1.36 mmol) were then added. The mixture was heated to 100 DC for 1 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04. filtered and concentrated in vacuo. Purification by SFC (column: 2-Ethylpyridine 5 muetaiota, 250 x 30 mm, 60A, Princeton; eluent: 10percent MeOH/C02 for 1 min, then from 10percent MeOH/C02 to 15percent MeOH/C02 in 6 min; then from 15percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) afforded the title compound (42 mg) as beige powder. UPLC-MS: MS 400.2 (M+H+); UPLC rt 0.86 min. 1H NMR (400 MHz, CHLOROFORM- : delta ppm 0.61 – 0.82 (m, 2 H); 0.82 – 0.91 (mr 2 H); 1.78 – 1.96 (m, 1 H); 2.56 (s, 3 H); 3.16 (t, J=6.02 Hz, 2 H); 3.89 (t, J=6.15 Hz, 2 H); 4.37 (br. s., 2 H); 6.62 (s, 1 H); 7.19 (d, J=1.25 Hz, 1 H); 7.38 – 7.48 (m, 1 H); 7.63 – 7.70 (m, 2 H); 7.78 (dd, J=7.65, .13 Hz, 1 H); 7.89 (d, J=1.26 Hz, 1 H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
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