Ammonia → (4s)-4-[5-(Benzothien-5-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7](B3OC(C)(C)C(C)(C)O3)[CH:8]=[CH:9][C:2]1=2.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=C([C:46]2[S:50][C:49]([O:51][C@@H:52]3[CH:59]4[CH2:60][N:55]5[CH2:56][CH:57]([CH2:61][CH:53]3[CH2:54]5)[CH2:58]4)=[N:48]C=2)C=N1.[NH3:62]>>[C:19]1([CH3:29])[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:26])=[O:27])=[CH:23][CH:24]=1.[S:1]1[C:2]2[CH:9]=[CH:8][C:7]([C:46]3[S:50][C:49]([O:51][C@@H:52]4[CH:59]5[CH2:60][N:55]6[CH2:56][CH:57]([CH2:61][CH:53]4[CH2:54]6)[CH2:58]5)=[N:48][N:62]=3)=[CH:6][C:3]=2[CH:4]=[CH:5]1Participants
4
Reactant 3
Product 1
Procedure
The free base of the title compound was prepared from the product of Example 41B (193 mg, 0.60 mmol) and 2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (317 mg, 0.74 mmol; Maybridge) 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 1.96 (d, J=12.5 Hz, 2H), 2.19 (s, 1H), 2.33 (d, J=13.6 Hz, 2H), 2.36 (s, 3H), 2.64 (s, 2H), 3.52-3.77 (m, 6H), 5.36 (s, 1H), 7.22 (d, J=8.8 Hz, 2H), 7.49 (d, J=5.4 Hz, 1H), 7.67-7.75 (m, 3H), 7.85 (dd, J=8.4, 1.7 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.32 (d, J=1.7 Hz, 1H). MS (DCI/NH3) m/z=370 (M+H)+. Anal. Calcd. for C19H19N3OS2.C7H8O3S: C, 57.65; H, 5.02; N, 7.76. Found: C, 56.45; H, 4.59; N, 7.45.
Sources & evidence
- ORD record
- ord-aafe1c2a72614e3ea895bac54419f4fe
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987453B2
Reaction notes
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