HCID 68774888, compound → HCID 11399357, compound

HRID 1726136Notes

Reaction equation

HRID 1726136 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH:8]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:19])[CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]1.[CH3:30][C:31]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[CH:37]=[C:36]([CH3:46])[C:32]=1[C:33](O)=[O:34]>>[CH3:46][C:36]1[CH:37]=[C:38]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[CH:39]=[C:31]([CH3:30])[C:32]=1[C:33]([NH:18][CH2:17][CH2:16][CH:15]([N:12]1[CH2:11][CH2:10][CH:9]([CH:8]([O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)[CH3:19])=[O:34]

Participants

3

Reactant 2

HCID 68774888HCID 68774888, compoundHCID 68971037HCID 68971037, compound

Product 1

HCID 11399357HCID 11399357, compoundYield 50.4%

Procedure

Using general procedure E, 3-{4-[(pyridin-2-yloxy)-(4-trifluoromethyl-phenyl)-methyl]-piperidin-1-yl}-butylamine (75 mg, 0.18 mmol) (see EXAMPLE 22) and 2,6-dimethyl-4-pyridin-4-yl-benzoic acid (46 mg, 0.20 mmol) gave COMPOUND 49 as a white solid (56 mg, 50%). 1H NMR (CDCl3) δ 0.46-1.09 (m, 2H), 0.94 (dd, 3H, J=6.6, 3.6 Hz), 1.44-2.05 (m, 5H), 2.24-2.46 (m, 1H), 2.40 (s, 3H), 2.41 (s, 3H), 2.54-2.89 (m, 4H), 3.23-3.40 (m, 1H), 3.77-3.94 (m, 1H), 5.23-5.31 (m, 1H), 6.60 (dd, 1H, J=8.4, 3.6 Hz), 6.54 (dd, 1H, J=11.7, 4.8 Hz), 7.17 (d, 2H, J=8.1 Hz), 7.36-7.44 (m, 5H), 5.54-5.57 (m, 2H), 7.84, 7.79 (dd, 1H, J=4.8, 1.2 Hz), 8.57, 8.73 (d, 1H, J=5.7 Hz), 8.61, 8.63 (s, 2H). 13C NMR (CDCl3) δ 13.22, 13.39, 19.40 (2 carbons), 28.23, 28.80, 29.09, 29.77, 30.52, 31.09, 39.72, 39.85, 42.21, 43.98, 51.97, 52.14, 60.25, 60.55, 79.55, 79.63, 111.01, 116.96, 121.67, 124.05 (q, J=272 Hz), 124.91, 124.95, 126.05, 126.07, 127.25, 129.46 (q, J=32 Hz), 135.18, 138.06, 138.16, 138.54, 139.39, 144.59, 144.67, 146.64, 147.88, 150.27, 162.79, 162.82, 169.26, 169.52. ES-MS m/z 617 (M+H). Anal. Calcd. for C36H39F3N4O2: C, 68.76; H, 6.36; N, 8.88; F, 9.04. Found. C, 68.54; H, 6.31; N, 8.75; F, 9.26.

Sources & evidence

ORD record
ord-46f82bf7365f490b84d00dd19c4d6ad5
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

Loading…