Ammonia → (4s)-4-[5-(Pyrazol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane bis(p-toluenesulfonate)
Reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2[S:29][C:28]([O:30][C@@H:31]3[CH:38]4[CH2:39][N:34]5[CH2:35][CH:36]([CH2:40][CH:32]3[CH2:33]5)[CH2:37]4)=[N:27][N:26]=2)[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1.[C:52]1([CH3:62])[CH:57]=[CH:56][C:55]([S:58]([OH:61])(=[O:60])=[O:59])=[CH:54][CH:53]=1.N1C=C(C2SC(O[C@@H]3C4CN5CC(CC3C5)C4)=NC=2)C=N1.N>>[C:41]1([CH3:51])[CH:42]=[CH:43][C:44]([S:47]([OH:50])(=[O:48])=[O:49])=[CH:45][CH:46]=1.[C:52]1([CH3:62])[CH:53]=[CH:54][C:55]([S:58]([OH:61])(=[O:59])=[O:60])=[CH:56][CH:57]=1.[NH:21]1[CH:22]=[C:23]([C:25]2[S:29][C:28]([O:30][C@@H:31]3[CH:32]4[CH2:33][N:34]5[CH2:35][CH:36]([CH2:37][CH:38]3[CH2:39]5)[CH2:40]4)=[N:27][N:26]=2)[CH:24]=[N:20]1Participants
4
Reactant 3
Product 1
Procedure
The free base of the title compound was prepared from the product of Example 54A (100 mg, 0.18 mmol) according to Method L, and then converted to the p-toluenesulfonate salt using the procedure of Method H: 1H NMR (300 MHz, methanol-D4) δ ppm 1.99 (d, J=13.6 Hz, 2H), 2.21 (s, 1H), 2.32 (s, 2H), 2.36 (s, 3H), 2.73 (s, 2H), 3.52-3.81 (m, 6H), 5.52 (s, 1H), 7.23 (d, J=8.1 Hz, 2H), 7.71 (d, J=8.1 Hz, 2H), 8.09 (br. s, 2H), MS (DCI/NH3) m/z=304 (M+H)+. Anal. Calcd. for C14H17N5OS.C7H8O3S: C, 53.03; H, 5.30; N, 14.73. Found: C, 52.48; H, 5.03; N, 14.46.
Sources & evidence
- ORD record
- ord-11761624b81847b58d120c1406499cea
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314119B2
Reaction notes
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