Ammonia → (4s)-4-[5-(1H-Indol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane p-toluensulfonate

HRID 878430Notes

Reaction equation

HRID 878430 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5](B(O)O)[C:4]=2[CH:3]=[CH:2]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=C([C:40]2[S:44][C:43]([O:45][C@@H:46]3[CH:53]4[CH2:54][N:49]5[CH2:50][CH:51]([CH2:55][CH:47]3[CH2:48]5)[CH2:52]4)=[N:42]C=2)C=N1.[NH3:56]>>[C:13]1([CH3:23])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[NH:1]1[C:9]2[C:4](=[C:5]([C:40]3[S:44][C:43]([O:45][C@@H:46]4[CH:53]5[CH2:54][N:49]6[CH2:50][CH:51]([CH2:55][CH:47]4[CH2:48]6)[CH2:52]5)=[N:42][N:56]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27631731H-Indole-4-boronic acidHCID 86621339(4s)-4-[5-(Pyrazol-4-yl)-thiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane bis (p-toluenesulfonate)

Product 1

HCID 86681396(4s)-4-[5-(1H-Indol-4-yl)-1,3,4-thiadiazol-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane p-toluensulfonate

Procedure

The free base of the title compound was prepared from the product of Example 41B (190 mg, 0.60 mmol) and indole-4-boronic acid (192 mg, 1.19 mmol; Frontier) 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=13.5 Hz, 2H), 2.36 (s, 3H), 2.64 (s, 2H), 3.52-3.77 (m, 6H), 5.36 (s, 1H), 7.04 (d, J=3.0 Hz, 1H), 7.17-7.27 (m, 3H), 7.43 (d, J=3.4 Hz, 1H), 7.49 (d, J=6.7 Hz, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H). MS (DCI/NH3) m/z=354 (M+H)+. Anal. Calcd. for C19H20N4OS.C7H8O3S: C, 59.92; H, 5.38; N, 10.68. Found: C, 56.90; H, 5.11; N, 10.13.

Sources & evidence

ORD record
ord-21bdcab5a83545f0b39ddd8f90861318
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

Loading…