p-Toluenesulfonic acid → 3-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane bis(4-methylbenzenesulfonate)

HRID 914762Notes

Reaction equation

HRID 914762 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][NH:11][CH2:12]3)[CH2:8]2)[CH:2]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[CH3:26][C:16]1[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1.[CH3:26][C:16]1[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:8][CH:9]3[CH2:15][CH:13]([CH2:12][NH:11][CH2:10]3)[CH2:14]2)[CH:2]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 99206863-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 865904043-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane bis(4-methylbenzenesulfonate)Yield 53%

Procedure

The product from Example 57A was treated with p-toluenesulfonic acid (2.0 eq) and the obtained solid recrystallized from ethanol/ether to provide the title compound (53% yield). 1H NMR (CD3OD, 300 MHz) δ 2.04 (m, 2H), 2.37 (s, 6H), 2.39 (m, 2H), 3.23 (m, 2H), 3.31 (m, 2H), 3.59 (bd, J=13.24 Hz, 2H), 4.04 (bd, 12.14 Hz, 2H), 7.23 (d, J=8.09 Hz, 4H), 7.67(d, J=8.09 Hz, 4H), 7.88 (dd, J=5.52, 8.83 Hz, 1H), 8.20-8.24(m, 2H), 8.50 (d, J=2.57 Hz, 1H); MS (DCI/NH3) m/z 204 (M+H)+; Anal. calculated for C12H17N3.2.2 TsOH.H2O C, 56.01; H, 6.04; N, 7.15. Found: C, 56.25; H, 6.10; N, 6.79.

Workup

  1. customthe obtained solid recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-843e0f8431624ec3a31474055844a551
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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