Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 71239514, compound

Participants

Reaction Steps

To a solution of 4-[3-Methyl-1-(7-methyl-quinolin-3-ylamino)-butyl]-benzoic acid (44 mg, 0.13 mM) in DCM (1 mL) was added TEA (63.6 mg, 0.629 mM) and followed by 3-amino-propionic acid methyl ester hydrochloric acid (6) (26.4 mg, 0.189 mM) and then HBTU (57.3 mg, 0.151 mM). The reaction was stirred at RT for 16 h. The reaction mixture was diluted with EtOAc (5 mL) and washed with water (2×2 mL). The organic layer was separated, dried over Na2SO4 and concentrated. The crude material was separated by a 12 g silica gel column with 10-100% EtOAc in heptane to afford desired product (49 mg, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 0.98 (d, J=6.10 Hz, 3 H) 1.04 (d, J=6.34 Hz, 3 H) 1.61-1.70 (m, 1 H) 1.71-1.86 (m, 2 H) 2.66 (t, 2 H) 2.82 (s, 3 H) 3.68-3.76 (m, 5 H) 4.36 (d, J=4.88 Hz, 1 H) 4.44-4.54 (m, 1 H) 6.73 (d, J=2.20 Hz, 1 H) 6.80 (t, J=5.49 Hz, 1 H) 7.20 (d, J=8.29 Hz, 1 H) 7.35 (d, J=8.54 Hz, 1 H) 7.45 (d, J=8.29 Hz, 2 H) 7.67 (s, 1 H) 7.75 (d, 2 H) 8.45 (d, J=2.44 Hz, 1 H). LC-MS: 434.2 (M+1).

Provenance & Evidence