Water → HCID 66696899, compound

Participants

Reaction Steps

A mixture of 4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexanecarbaldehyde (39 mg), morpholine (14 μL) and acetic acid (2 drops) in DCE (2 mL) was stirred at RT for 2 hours; sodium triacetoxyborohydride was then added. The resulting mixture was stirred for 3 hours at RT. Water was added; the organic layer was separated and washed 3 times with water. The aqueous layer was re-extracted with DCM. The combined organic extracts were dried over Na2SO4 and filtered; the solvent was evaporated under reduced pressure and the residue was purified via preparative TLC to afford 13.2 mg of (4-benzotriazol-1-yl-pyrimidin-2-yl)-(4-morpholin-4-ylmethyl-cyclohexyl)-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.56 (1 H, d, J=8.31 Hz), 8.36-8.46 (1 H, bd), 8.12 (1 H, d, J=8.31 Hz), 7.55-7.69 (1 H, m), 7.40-7.52 (2H, m), 5.22-5.64 (1 H, m), 3.49-3.96 (5 H, m), 2.12-2.56 (6 H, m), 1.46-2.04 (5 H, m), 1.03-1.46 (4 H, m).

Provenance & Evidence