4,6-Dimethylpyrimidine-5-carboxylic acid → HCID 57563210, compound

HRID 1726269Notes

Reaction equation

HRID 1726269 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:18]3[CH2:23][CH2:22][N:21]([CH:24]([CH3:28])[CH2:25][CH2:26][NH2:27])[CH2:20][CH2:19]3)[O:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10]2)=[CH:5][CH:4]=1.[CH3:29][C:30]1[C:35]([C:36](O)=[O:37])=[C:34]([CH3:39])[N:33]=[CH:32][N:31]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:18]3[CH2:23][CH2:22][N:21]([CH:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:36]([C:35]4[C:30]([CH3:29])=[N:31][CH:32]=[N:33][C:34]=4[CH3:39])=[O:37])[CH2:20][CH2:19]3)[O:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68971734HCID 68971734, compound

Product 1

HCID 57563210HCID 57563210, compoundYield 63%

Procedure

Using general procedure E, 3-{4-[2-(4-methoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidin-1-yl}-butylamine (see EXAMPLE 284) (50 mg, 0.13 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (24 mg, 0.16 mmol) afforded COMPOUND 285 as a white solid (42 mg, 63%). 1H NMR (CDCl3) δ 0.70-0.84 (m, 1H), 0.94 (d, 3H, J=6.6 Hz), 0.95-1.08 (m, 1H), 1.45-1.63 (m, 3H), 1.66-1.80 (m, 1H), 1.86-1.98 (m, 2H), 2.38 (t, 1H, J=11.4 Hz), 2.52 (s, 6H), 2.66-2.84 (m, 3H), 3.22-3.31 (m, 1H), 3.79 (s, 3H), 3.87-3.97 (m, 1H), 6.74-6.79 (m, 2H), 6.83-6.88 (m, 3H), 6.91-6.94 (m, 1H), 7.29 (d, 2H, J=9.0 Hz), 8.86-8.88 (m, 1H), 9.08 (s, 1H). 13C NMR (CDCl3) δ 13.37, 22.07, 25.89, 26.55, 30.77, 40.43, 43.83, 45.63, 52.47, 55.45, 60.96, 108.65, 108.73, 113.61, 118.42, 121.44, 126.99, 131.00, 131.96, 147.38, 147.50, 157.84, 159.96, 163.05, 166.71. ES-MS m/z 517 (M+H). Anal. Calcd. for C30H36N4O4.0.1CH2Cl2: C, 68.85; H, 6.95; N, 10.67. Found: C, 69.00; H, 7.03; N, 10.76.

Sources & evidence

ORD record
ord-0bb0ae94e7fa493d95930761ed3fc3b3
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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