Ammonia → (4s)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

HRID 1878648Notes

Reaction equation

HRID 1878648 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C@@H:9]2[CH:16]3[CH2:17][N:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)=[N:6][CH:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:33][CH:34]=1.N>>[C:29]1([CH3:28])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[C:19]1([C:2]2[CH:3]=[CH:4][C:5]([O:8][C@@H:9]3[CH:16]4[CH2:17][N:12]5[CH2:13][CH:14]([CH2:18][CH:10]3[CH2:11]5)[CH2:15]4)=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 66827Phenylboronic AcidHCID 24990114(4s)-4-(5-Bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane

Product 1

HCID 86621319(4s)-4-(5-Phenylpyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

Procedure

The free base of the title compound was prepared from the product of Example 10C (45 mg, 0.14 mmol) and phenylboronic acid (25 mg, 0.20 mmol) according to Method F, and converted to the p-toluenesulfonate salt using the procedure of Method H: 1H NMR (300 MHz, methanol-D4) δ ppm 1.94 (d, J=1.3.2 Hz, 2H), 2.20 (s, 1H), 2.36 (s, 5H), 2.41 (s, 1H), 2.57 (s, 2H), 3.58 (s, 2H), 3.70 (s, 4H), 5.47 (t, J=3.4 Hz, 1H), 7.09 (d, J=8.5 Hz, 1H), 7.22 (d, J=7.8 Hz, 2H), 7.30-7.41 (m, 1H), 742-7.51 (m, 2H), 7.56-7.63 (m, 2H), 7.67-7.75 (m, 2H), 8.07 (dd, J=8.6, 2.5 Hz, 1H), 8.40 (d, J=2.4 Hz, 1H). MS (DCI/NH3) m/z=307 (M+H)+; Anal. Calcd. for C20H22N2O.1.3C7H8O3S.0.5H2: C, 64.81; H, 6.24; N, 5.19. Found: C, 64.77; H, 630; N, 5.15.

Sources & evidence

ORD record
ord-cbed3ec4333041a6b7b60451da8d9c0e
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

Loading…