Methanol → HCID 24961040, compound

Participants

Reaction Steps

To a stirring solution of 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-amine (150 mg, 0.50 mmol) and 4-nitrophenyl thiazol-2-ylcarbamate (144 mg, 0.55 mmol) in DCM (5 mL) was added DIPEA (173 uL, 1.00 mmol) at RT. The mixture was allowed to stir for 15 h before the solution was concentrated in vacuo. Purification by prep TLC plate using 15:1 DCM:MeOH yielded the desired compound 1-(1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-yl)-3-(5-methylisoxazol-3-yl)urea (80 mg, 0.19 mmol, 38% yield). MS (ESI pos. ion) m/z: 426.2 (MH+). Calc'd exact mass for C22H27N5O4: 425. 1HNMR (400 MHz, CDCl3): 8.66-8.67 (d, J=4.4 Hz, 1H), 8.36 (bs, 1H), 7.60 (s, 1H), 7.45 (s, 1H), 7.27-7.28 (m, 1H, covered by residual solvent), 5.83 (s, 1H), 4.05 (s, 6H), 3.87 (s, 2H), 3.83-3.85 (m, 1H), 2.83-2.85 (bd, J=10.0 Hz, 2H), 2.37 (s, 3H), 2.31-2.36 (bt, J=10.4 Hz, 2H overlapping), 1.99-2.02 (bd, J=11.2 Hz, 2H), 1.58-1.66 (m, 2H).

Provenance & Evidence