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

HRID 1726253Notes

Reaction equation

HRID 1726253 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH:20]3[CH2:25][CH2:24][N:23]([CH:26]([CH3:30])[CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]3)[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[O:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:31][C:32]1[N:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:33]=1[C:34](O)=[O:35]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH:20]3[CH2:25][CH2:24][N:23]([CH:26]([CH3:30])[CH2:27][CH2:28][NH:29][C:34](=[O:35])[C:33]4[C:37]([CH3:41])=[CH:38][CH:39]=[N:40][C:32]=4[CH3:31])[CH2:22][CH2:21]3)[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[O:12]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 689687073-{4-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine

Product 1

HCID 57563090N-(3-{4-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butyl)-2,4-dimethyl-nicotinamideYield 32.7%

Procedure

Using general procedure E, 3-{4-[2-(4-methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine (see EXAMPLE 273) (139 mg, 0.32 mmol) and 2,4-dimethylnicotinic acid (53 mg, 0.35 mmol) afforded COMPOUND 274 as a white solid (59 mg, 32%). 1H NMR (CDCl3) δ 0.84-1.19 (m, 2H), 0.95 (d, 3H, J=6.6 Hz), 1.45-1.62 (m, 3H), 1.66-1.79 (m, 1H), 1.89-1.99 (m, 2H), 2.31 (s, 3H), 2.36 (t, 1H, J=11.7 Hz), 2.54 (s, 3H), 2.68-2.81 (m, 3H), 3.02 (s, 3H), 3.26-3.34 (m, 1H), 3.49 (s, 2H), 3.80-3.89 (m, 1H), 6.78-6.88 (m, 3H), 7.00 (d, 1H, J=4.8 Hz), 7.60 (d, 2H, J=8.1 Hz), 7.91 (d, 2H, J=7.8 Hz), 8.05 (br s, 1H), 8.42 (d, 1H, J=4.8 Hz). 13C NMR (CDCl3) δ 13.58, 19.20, 22.67, 25.88, 26.50, 31.68, 40.00, 44.24, 44.80, 45.65, 52.34, 60.55, 109.09, 117.67, 122.11, 122.92, 127.29, 127.63, 134.00, 141.22, 144.09, 146.41, 147.20, 149.23, 154.55, 168.70. ES-MS m/z 564 (M+H). Anal. Calcd. for C31H37N3O5S.1.0CH2Cl2.0.3H2O: C, 58.77; H, 6.10; N, 6.42. Found: C, 58.42; H, 5.79; N, 6.37.

Sources & evidence

ORD record
ord-90087f93da854c0aac4a9b2fa80be5fa
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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