Ammonia → (4s)-4-[(5-Thien-2-ylpyridin-2-yl)oxy]-1-azatricyclo[3.3.1.13,7]decane

HRID 878440Notes

Reaction equation

HRID 878440 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.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=C(C2SC(O[C@@H]3C4CN5CC(CC3C5)C4)=NN=2)C=N1.N>>[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[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

Participants

5

Reactant 4

HCID 222AmmoniaHCID 27339602-Thiopheneboronic acidHCID 24990114(4s)-4-(5-Bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decaneHCID 136406836(4s)-4-[5-(Pyrazol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane bis(p-toluenesulfonate)

Product 1

HCID 24986790(4s)-4-[(5-Thien-2-ylpyridin-2-yl)oxy]-1-azatricyclo[3.3.1.13,7]decane

Procedure

The free base of the title compound was prepared from the product of Example 10C (50 mg, 0.16 mmol) and 2-thiophene boronic acid (29 mg, 0.23 mmol; Aldrich) according to Method G, and converted to the p-toluenesulfonate salt using the procedure of Method H: 1H NMR (300 MHz, methanol-D4) δ ppm 1.92 (d, J=13.6 Hz, 2H), 2.19 (s, 1H), 2.32-2.46 (m, 6H), 2.55 (s, 2H), 3.57 (s, 2H), 3.68 (s, 4H), 5.46 (s, 1H), 6.93 (d, J=8.5 Hz, 1H), 7.10 (dd, J=5.1, 3.4 Hz, 1H), 7.22 (d, J=8.5 Hz, 2H), 7.37 (dd, J=15.3, 4.4 Hz, 2H), 7.70 (d, J=8.1 Hz, 2H), 7.97 (dd, J=8.6, 2.5 Hz, 1H), 8.38 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/z=313 (M+H)+.

Sources & evidence

ORD record
ord-935fcdbb2afe4e7f8c1a7181e3fff447
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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