Triethylamine → 7-Chloro-N-[1-(phenylmethyl)-4-piperidinyl]-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]-carbonyl]phenyl]amino]-3-quinolinecarboxamide

Participants

Reaction Conditions

Reaction Steps

Step 5, 7-Chloro-N-[1-(phenylmethyl)-4-piperidinyl]-4-[[4-[[[1-(phenylmethyl) -4-piperidinyl]]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide: 7-Chloro -4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]-carbonyl]phenyl]amino]-3-quinolinecarboxylic acid (2.00 g, 3.88 mmol), 1-hydroxybenzotriazole hydrate (0.640 g, 4.74 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.968 g, 5.05 mmol) were stirred in 22 ml of DMF and treated with triethylamine (1.57 g, 2.2 ml, 15.5 mmol) followed by 4-amino-1-benzylpiperidine (0.813 g, 0.87 ml, 4.27 mmol). The reaction mixture was then heated at 90° C. under nitrogen for 4 h, cooled to room temperature and poured into 250 ml of CH2CH2. The solution was then washed with 3×200 ml of water and concentrated under reduced pressure to a pale beige powder that was dried in vacuo overnight affording 2.037 g (2.96 mmol, 76% yield) of 7-Chloro-N-[1-(phenylmethyl)-4-piperidinyl]-4-[[4-[[[1-(phenylmethyl) -4-piperidinyl]amino]-carbonyl]phenyl]amino]-3-quinolinecarboxamide: mp 230.5°-232° C.; IR (KBr) 3440, 3330, 30 30, 2950, 2800, 1630 cm-1 ; 1H NMR (Me2SO-d6, 400 MHz) δ 9.7 (s, 1 H ), 8.8 (s, 1 H ), 8.39 (d, J=7.5 Hz, 1 H ), 8.11 (d, J=9.1 Hz, 1 H), 8.0 (m, 2 H ), 7.7 (d, J=8.7 Hz, 2 H ), 7.6 (d of d, J=2.2, 9.1 Hz, 1 H ), 7.1-7.35 (m, 10 H ), 6.9 (d, J=8.7 Hz, 2 H ), 3.7 (m, 1 H ), 3.4 (m, 5 H ), 2.74°-2.82 (m, 2 H), 2.64-2.7 (m, 2 H), 1.84-2.04 (m, 4 H ), 1.64°-1.72 (m, 2 H ), 1.46-1.58 (m, 4 H), 1.3-1.4 (m, 2 H ); MS (+DCI, isobutane) m/z (rel intensity)=687 (M+, 100).

Provenance & Evidence