Reference of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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 solution of the desired intermediate 3a-l (0.07 mmol, 1 eq) in 1 mL DMSO was taken in a 5mL sealed reaction vessel, the corresponding amine (trans-4-aminocyclohexanol for 4a-k) (0.212 mmol, 3 eq) then diisopropylethylamine (DIPEA)(0.2l2 mmol, 3eq) was introduced. The reaction vessel was then sealed and heated to 140 C for 12 h, cooled and water (25 mL) was added. The aqueous layer was extracted with ethyl acetate (25 mL X 3), the organic fractions were combined and washed with brine (25mL) and dried over sodium sulfate. Purification with column chromatography (S1O2, 4:96 methanokDCM for 4a-k, 5a,5b,5e and 5: 1 :94 methanol :7M NH3 in methanokDCM for 5c,5d,5f,5g) resulted in the desired products which were further purified by preparative TLC to give the desired compounds 4a-k, 5a-g as light yellow solids. 8-(((lr,4r)-4-hydroxycyclohexyl)amino)-3-methyl-6-(3,6,6-trimethyl-4-oxo- 4,5,6,7-tetrahydro-lH-indazol-l-yl)isoquinolin-l(2H)-one (4a): 22 mg, Yield 70%; NMR (400 MHz, Chloroform -if) d 9.16 (d, J= 7.5 Hz, 1H), 9.05 (s, 1H), 6.51 – 6.40 (m, 2H), 6.09 (s, 1H), 3.74 – 3.59 (m, 2H), 3.31 (d, j= 24.2 Hz, 1H), 2.78 (s, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 2.19 (s, 3H), 2.17 – 2.08 (m, 2H), 2.04 – 1.95 (m, 2H), 1.38 (q, 7= 11.1, 9.9 Hz, 4H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCh) d 193.4, 185.3, 169.7, 165.5, 151.4, 150.0, 149.1, 143.5, 143.2, 142.1, 137.4, 107.3, 105.7, 104.8, 100.3, 69.7, 52.4, 50.2, 37.8, 35.8, 33.5, 29.9, 28.4 (2), 19.0, 13.4. HRMS (ESI) m/z [M+H] calculated for C26H33N4O3, 449.2553, found 449.2566.
The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; BLAGG, Brian; SANKET, Mishra; (0 pag.)WO2019/232223; (2019); A1;,
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