2,4-Dimethyl-3-pyridinecarboxylic acid → 2,4-Dimethyl-N-(3-{4-[2-(4-trifluoromethoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butyl)-nicotinamide

HRID 1726256Notes

Reaction equation

HRID 1726256 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:29])[CH2:26][CH2:27][NH2:28])[CH2:21][CH2:20]3)[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)=[CH:6][CH:5]=1.[CH3:32][C:33]1[N:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35](O)=[O:36]>>[CH3:32][C:33]1[N:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35]([NH:28][CH2:27][CH2:26][CH:25]([N:22]1[CH2:21][CH2:20][CH:19]([C:10]2([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=3)[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:24][CH2:23]1)[CH3:29])=[O:36]

Participants

3

Reactant 2

HCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 689729793-{4-[2-(4-Trifluoromethoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine

Product 1

HCID 575630632,4-Dimethyl-N-(3-{4-[2-(4-trifluoromethoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butyl)-nicotinamideYield 31.1%

Procedure

Using general procedure E, 3-{4-[2-(4-trifluoromethoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine (see EXAMPLE 275) (135 mg, 0.31 mmol) and 2,4-dimethylnicotinic acid (51 mg, 0.34 mmol) afforded COMPOUND 276 (55 mg, 31%). 1H NMR (CDCl3) δ 0.83-1.17 (m, 2H), 0.95 (d, 3H, J=6.6 Hz), 1.46-1.63 (m, 3H), 1.67-1.80 (m, 1H), 1.86-1.99 (m, 2H), 2.31 (s, 3H), 2.33-2.40 (m, 1H), 2.54 (s, 3H), 2.67-2.81 (m, 3H), 3.25-3.35 (m, 1H), 3.79-3.89 (m, 1H), 6.76-6.86 (m, 4H), 6.99 (d, 1H, J=5.1 Hz), 7.17 (d, 2H, J=8.1 Hz), 7.40-7.44 (m, 2H), 8.11 (br s, 1H), 8.42 (d, 1H, J=4.8 Hz). 13C NMR (CDCl3) δ 13.57, 19.19, 22.63, 25.94, 26.56, 31.64, 40.02, 44.32, 45.92, 52.42, 60.54, 108.92, 118.07, 120.78, 121.86, 122.91, 127.68, 133.99, 138.89, 144.02, 147.35, 149.21, 149.76, 154.55, 168.73. ES-MS m/z 570 (M+H). Anal. Calcd. for C31H34N3F3O4.0.28CH2Cl2: C, 63.31; H, 5.87; N, 7.08. Found: C, 63.01; H, 5.88; N, 7.47.

Sources & evidence

ORD record
ord-ef1b406715174b558f497b36f95f490e
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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