4,6-Dimethylpyrimidine-5-carboxylic acid → HCID 57563131, compound

HRID 1726243Notes

Reaction equation

HRID 1726243 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][C:9]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]([CH3:31])[CH2:28][CH2:29][NH2:30])[CH2:23][CH2:22]3)([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:32][C:33]1[C:38]([C:39](O)=[O:40])=[C:37]([CH3:42])[N:36]=[CH:35][N:34]=1>>[F:1][C:2]1[C:7]2[CH2:8][C:9]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]([CH3:31])[CH2:28][CH2:29][NH:30][C:39]([C:38]4[C:33]([CH3:32])=[N:34][CH:35]=[N:36][C:37]=4[CH3:42])=[O:40])[CH2:23][CH2:22]3)([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=3)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68968989HCID 68968989, compound

Product 1

HCID 57563131HCID 57563131, compoundYield 41%

Procedure

Using general procedure E, 3-{4-[4-fluoro-2-(4-trifluoromethyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidin-1-yl}-butylamine (see EXAMPLE 251) (60 mg, 0.14 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (42 mg, 0.28 mmol) afforded COMPOUND 257 as a white solid (32 mg, 41%). 1H NMR (CDCl3) δ 0.62-0.92 (m, 2H), 0.92-0.97 (m, 3H), 1.09-1.23 (m, 1H), 1.50-1.55 (m, 1H), 1.69-1.78 (m, 2H), 1.84-2.02 (m, 2H), 2.24-2.45 (m, 1H), 2.50 (s, 6H), 2.61-2.86 (m, 3H), 3.17-3.47 (m, 3H), 3.70-4.00 (m, 1H), 6.51-6.57 (m, 1H), 6.84, 6.89 (d, 1H, J=8.1 Hz), 7.10-7.17 (m, 1H), 7.36-7.43 (m, 2H), 7.58-7.62 (m, 2H), 8.44, 8.59 (m, 1H), 9.04, 9.09 (s, 1H). 13C NMR (CDCl3) δ 14.55, 14.95, 23.47, 27.69, 28.14, 28.30, 29.01, 31.91, 32.79, 38.48, 38.90, 41.46, 41.67, 45.53, 45.79, 48.46, 48.52, 53.92, 54.00, 61.60, 62.16, 94.67, 94.84, 107.08, 109.15, 109.42, 113.35, 113.62, 123.78, 126.91, 127.05, 127.16, 127.39, 131.29, 131.40, 131.48, 132.30, 150.24, 150.40, 158.92, 159.20, 162.19, 162.56, 164.50, 167.87, 168.26. ES-MS m/z 571 (M+H). Anal. Calcd. for C31H34N4O2F4.0.5H2O: C, 64.24; H, 6.09; N, 9.67. Found: C, 64.25; H, 6.00; N, 9.68.

Sources & evidence

ORD record
ord-4ae73d7467c64f77b4227359b23938da
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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