2,4-Dimethylpyridine-3-carboxylic acid--hydrogen chloride (1/1) → HCID 57563255, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:28]=2[CH3:29])[C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[CH3:5].Cl.[CH3:31][C:32]1[N:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:33]=1[C:34](O)=[O:35]>>[C:17]([C:16]1[CH:20]=[CH:21][C:13]([N:12]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:28]=2[CH3:29])[CH:9]2[CH2:10][CH2:11][N:6]([CH:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:34](=[O:35])[C:33]3[C:37]([CH3:41])=[CH:38][CH:39]=[N:40][C:32]=3[CH3:31])[CH2:7][CH2:8]2)=[CH:14][CH:15]=1)(=[O:18])[NH2:19]Participants
Procedure
Using general procedure E, 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-amino]-benzamide (see EXAMPLE 355) (21.8 mg, 0.055 mmol) and 2,4-dimethylnicotinic acid hydrochloride (15 mg, 0.080 mmol) gave COMPOUND 366 as an off-white solid (24.6 mg, 84%). 1H NMR (CDCl3) δ 1.03 (d, 3H, J=6.6 Hz), 1.09-1.38 (m, 2H), 1.53-1.63 (m, 1H), 1.72-1.90 (m, 3H), 2.24 (t, 1H, J=11.0 Hz), 2.29 (s, 3H), 2.39 (s, 3H), 2.53 (s, 3H), 2.59 (t, 1H, J=11.0 Hz), 2.74-2.93 (m, 3H), 3.31-3.42 (m, 1H), 3.71-3.84 (m, 2H), 4.12 (s, 2H), 5.64 (br s, 2H), 6.53 (d, 2H, J=8.9 Hz), 6.84 (d, 1H, J=5.0 Hz), 7.12 (d, 1H, J=4.9 Hz), 7.61 (d, 2H, J=8.9 Hz), 7.65 (br s, 1H), 8.18 (s, 1H), 8.18 (d, 1H, J=5.0 Hz), 8.37 (d, 1H, J=4.9 Hz). 13C NMR (CDCl3) δ 13.44, 18.65, 18.72, 22.26, 29.28, 30.17, 31.72, 39.11, 44.05, 44.86, 51.61, 56.13, 59.29, 112.07, 121.24, 122.44, 125.08, 129.13, 131.84, 133.50, 143.83, 144.19, 147.41, 148.19, 148.63, 150.95, 154.03, 168.20, 169.02. ESI-MS m/z 529 (MH)+. Anal. Calcd. for C31H40N6O2.0.6CH2Cl2: C, 65.48; H, 7.16; N, 14.50. Found: C, 65.26; H, 7.46; N, 14.25.
Sources & evidence
- ORD record
- ord-8da22e79d41d4701afbdf2f084ba436f
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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