Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 28539-02-8, name is 1-(Hydroxymethyl)benzotriazole. A new synthetic method of this compound is introduced below., Formula: C7H7N3O
To a solution of 3 ,4,6-trimethyl-2-(5 -((1 -methylcyclopropyl)methoxy)-2-azabicyclo[4. 1. Ojheptan-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-bjpyridin-5-one (77 mg, 0.217 mmol) in THF (1 mL) was added LiHMDS (1.083 ml, 1.083 mmol) at -78C. Then the mixture was stirred at -78 C for 30 mm. Then(1H-benzo[dj[1,2,3jtriazol-1-yl)methanol (48.5 mg, 0.325 mmol) in THF (1 mL) was dropwise added to the mixture and the mixture was stirred for another 30 mm. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (10 mLx 2). The combined organic layers were dried over Na2504 and filtered, and the filtrate was concentrated in vacuo to give the residue, which was further purified by prep-TLC (dichloromethane : MeOH = 10:1) to provide the title compound as yellow oil. The title compound was separated by chiral SFC (AD(250mm*3Omm,lOum), 30% MeOH with 0.1%NH3.H20/C02 at 6OmL/min) and Prep-HPLC (TFA) to give four isomers. Example 5 (firstpeak): MS: 386.1 (M+1). ?H NMR (400 MHz, Methanol-d4): oe 4.23-4.25 (1 H, m), 4.11-4.14 (2H, m), 3.97-3.99 (1 H, m), 3.79-3.82 (1 H, m), 3.46-3.49 (1 H, m), 3.33-3.35 (1 H, m), 3.13 (3H, s), 2.94-3.01 (2 H, m), 2.60 (3 H, s), 2.36 (3 H, s), 1.95-2.01 (1 H, m), 1.46-1.70 (2 H, m),1.14 (3 H, s), 0.87-0.92 (1 H, m), 0.58-0.61 (1 H, m), 0.42-0.45 (2 H, m), 0.30-0.32 (2 H, m).Example 6 (second peak): MS: 386.2 (M+1). ?H NMR (400 MHz, Methanol-d4): oe 4.23-4.25 (1H, m), 4.11-4.14 (2 H, m), 4.01-4.04 (1 H, m), 3.79-3.82 (1 H, m), 3.46-3.49 (1 H, m), 3.32-3.35(1 H, m), 3.13 (3 H, s), 2.94-3.01 (2 H, m), 2.60 (3 H, s), 2.36 (3 H, s), 1.95-2.01 (1 H, m), 1.46-1.70 (2 H, m), 1.14 (3 H, s), 0.87-0.92 (1 H,m), 0.58-0.61 (1 H, m), 0.42-0.45 (2 H, m), 0.30-0.32 (2 H, m). Example 7 (third peak): MS: 386.2 (M+1). ?H NMR (400 MHz, Methanol-d4): oe4.23-4.25(1 H, m), 4.11-4.14(2 H, m), 4.01-4.02 (1 H, m), 3.79-3.82 (1 H, m), 3.45-3.47(1 H,m), 3.32-3.35 (1 H, m), 3.13 (3 H, s), 2.94-3.01 (2 H, m), 2.60 (3 H, s), 2.36 (3 H, s), 1.95-2.01(1 H, m), 1.46-1.70 (2 H, m), 1.14 (3 H, s), 0.87-0.92 (1 H, m), 0.58-0.61 (1 H, m), 0.42-0.45 (2H, m), 0.3 1-0.32 (2 H, m). Example 8 (fourth peak): MS: 386.1 (M+1).?H NMR (400 MHz,Methanol-d4): oe 4.23-4.26(1 H, m), 4.11-4.14(2 H, m), 3.98-4.01 (1 H, m), 3.79-3.82(1 H, m), 3.45-3.47 (1 H, m), 3.32-3.35 (1 H, m), 3.13 (3 H, s), 2.94-3.01 (2 H, m), 2.60 (3 H, s), 2.36 (3 H, s), 1.95-2.01 (1 H, m), 1.46-1.70 (2 H, m), 1.14 (3 H, s), 0.87-0.92 (1 H, m), 0.58-0.61 (1 H, m), 0.42-0.44 (2 H, m), 0.3 1-0.32 (2 H, m).
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Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane James; FELLS, James, I.; KOZLOWSKI, Joseph, A.; LIU, Ping; MAZZOLA, Robert, D., Jr.; (94 pag.)WO2018/226545; (2018); A1;,
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