Application of 41566-77-2, A common heterocyclic compound, 41566-77-2, name is 5-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride, molecular formula is C10H14ClNO, 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.
To the solution of 5-methoxy-indan-1-ylamine hydrochloride (92 mg, 0.46 mmol) and (3- cyclopropyl-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (buildingblock A7, 120 mg, 0.46 mmol) in DMF (6 ml) were added DIPEA (0.24 ml, 1.38 mmol) and HATU (210 mg, 0.55 mmol) and the reaction was stirred at rt for 30 min. The mixture was diluted with EtOAc, washed with aqueous bicarbonate solution and brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. Purification by preparative HPLC (Gilson GX-281 , Waters Sunfire C18, 5muetaeta, 30 x 100 mm with guard column 19 x 10 mm, solvent A: water with 0.1% TFA, solvent B: acetonitrile, gradient 40-60% B in 15 min, flow reate 50 ml/min) gave the title compound as colorless solid (140 mg, 75%). [1 H-NMR (DMSO-de, 600 MHz) delta 8.40 (d, 1 H), 7.02 (d, 1 H), 6.81 (s, 1 H), 6.68 (d, 1 H), 6.48 (s, 1 H), 5.26 (dd, 1 H), 4.80 (s, 2H), 3.76 (s, 3H), 3.71 (s, 3H), 2.91-2.88 (m, 1 H), 2.78-2.73 (m, 1 H), 2.66 (s, 3H), 2.38-2.33 (m, 1 H), 2.28-2.24 (m, 1 H), 1.89-1.82 (m, 1 H), 0.92-0.85 (m, 4H); LCMS RtH = 3.095 min; [M+H]+ = 407.2]
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; BADIGER, Sangamesch; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; CHEBROLU, Murali; COSTESTA, Simona; HINTERMANN, Samuel; MEYER, Arndt; PANDIT, Chetan; WO2011/76744; (2011); A1;,
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