HCID 68774888, compound → HCID 11215803, compound

HRID 1726137Notes

Reaction equation

HRID 1726137 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:20])[CH2:17][CH2:18][NH2:19])[CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[CH3:31][C:32]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)[CH:38]=[C:37]([CH3:47])[C:33]=1[C:34](O)=[O:35]>>[CH3:47][C:37]1[CH:38]=[C:39]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)[CH:40]=[C:32]([CH3:31])[C:33]=1[C:34]([NH:19][CH2:18][CH2:17][CH:16]([N:13]1[CH2:12][CH2:11][CH:10]([CH:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=2)[CH2:15][CH2:14]1)[CH3:20])=[O:35]

Participants

3

Reactant 2

HCID 68774888HCID 68774888, compoundHCID 68968703HCID 68968703, compound

Product 1

HCID 11215803HCID 11215803, compoundYield 50%

Procedure

Using general procedure E, 3-{4-[(6-methyl-pyridin-2-yloxy)-(4-trifluoromethyl-phenyl)-methyl]-piperidin-1-yl}-butylamine (see EXAMPLE 23) (40 mg, 0.10 mmol) and 2,6-dimethyl-4-pyridin-4-yl-benzoic acid (24 mg, 0.11 mmol) afforded COMPOUND 50 (30 mg, 50%). 1H NMR (CDCl3) δ 0.50-1.10 (m, 2H), 0.95, 0.96 (d, 3H, J=6.1 Hz), 1.47-2.06 (m, 5H), 2.20, 2.22 (s, 3H), 2.26-2.45 (m, 1H), 2.42 (s, 6H), 2.56-2.87 (m, 4H), 3.24-3.41 (m, 1H), 3.76-3.94 (m, 1H), 5.16, 5.23 (d, 1H, J=8.1 Hz), 6.29 (dd, 1H, J=8.4, 4.5 Hz), 6.57 (dd, 1H, J=7.5, 2.7 Hz), 7.18-7.24 (m, 3H), 7.36-7.40 (m, 4H), 7.50 (d, 2H, J=4.8 Hz), 8.35, 8.47 (br s, 1H), 8.61-8.64 (m, 2H). 13C NMR (CDCl3) δ 13.17, 13.39, 19.42, 23.99, 24.03, 28.26, 28.90, 29.08, 29.87, 30.78, 31.32, 39.58, 39.69, 42.28, 44.06, 44.16, 51.95, 52.10, 60.03, 60.38, 79.67, 79.83, 106.97, 107.01, 116.03, 121.47, 124.06 (q, J=272 Hz), 124.88, 124.92, 125.93, 127.35, 129.43 (q, J=32 Hz), 135.25, 137.90, 137.97, 138.77, 139.38, 144.73, 147.70, 150.32, 156.19, 162.20, 169.26, 169.54. ES-MS m/z 631 (M+H). Anal. Calcd. for C37H41F3N4O2: C, 70.06; H, 6.58; N, 8.83; F, 8.98. Found. C, 70.15; H, 6.50; N, 8.79; F, 8.78.

Sources & evidence

ORD record
ord-8e33ba552ca045c79dba7fc721066312
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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