Reference of 36805-97-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36805-97-7 as follows.
1 ,1-Di-tert-butoxy-W,A/-dimethylmethanamine (1.03 ml, 4.30 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1 -ethyl-1 H-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 39 (380 mg, 1.08 mmol) in toluene (10 ml). The reaction was heated at 80 C for 2 h then allowed to cool to RT. 1 ,1-Di-tert-butoxy-A/,/v- dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 80 C for 3 h then allowed to cool to RT. 1 ,1-Di-terf-butoxy-A/,W-dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 110 C for 1 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (20 ml) then washed with water (2 x 20 ml), saturated aq. NaHC03 solution (2 x 20 ml) and brine (10 ml), then dried over Na2S04, filtered and evaporated to afford an orange solid (510 mg). The crude material was purified by flash column chromatography on a silica column (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 0:100 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a white solid (320 mg, 72%).1H NMR (500 MHz, DMSO-de) delta 8.07 (s, 1 H), 7.98 (t, J = 5.8 Hz, 1 H), 7.77 (dd, J = 8.4, 1.3 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.41 – 7.12 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 5.9 Hz, 2H), 4.38 – 4.24 (m, 2H), 1.58 (s, 9H), 1.29 (t, J = 7.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 4 0 [MH+], R, = 1.17 min, UV purity = 99%.
According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.
Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem