Fumaric Acid → 5-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole Fumarate

HRID 1372845Notes

Reaction equation

HRID 1372845 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][CH:20]=[CH:19]4)=[CH:12][CH:11]=1)[CH2:2]2.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CCOC(C)=O.CCO>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][CH:20]=[CH:19]4)=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 113246115-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole

Product 1

HCID 210726145-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole Fumarate

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 3A (80 mg, 0.25 mmol) was treated with fumaric acid (29 mg, 0.25 mmol) in EtOAc/EtOH (v. 1:1, 4 mL) at ambient temperature for 10 h. The title compound was obtained as solid (57 mg, yield, 52%). 1H NMR (300 MHz, CD3OD) δ 1.78–2.16 (m, 3H), 2.25–2.39 (m, 1H), 2.46–2.54 (m, 1H), 3.14–3.45 (m, 5H), 3.69–3.81 (m, 1H), 4.80–4.89 (m, 1H), 6.46 (dd, J=3.0, 1.0, 1H), 6.68 (s, 2H), 7.02 (dt, J=8.8, 2.5 Hz, 2H), 7.23 (d, J=3.1 Hz, 1H), 7.31 (dd, J=8.5, 2.0 Hz, 1H), 7.43 (dt, J=8.4, 0.8 Hz, 1H), 7.58 (dt, J=9.2, 2.6 Hz, 2H), 7.71 (dd, J=1.7, 1.0 Hz, 1H) ppm. MS (DCl/NH3): m/z 319 (M+H)+. Anal. Calculated for C21H22N2O.C4H4O4: C, 69.11; H, 6.03; N, 6.45. Found: C, 69.23; H, 5.81; N, 6.59.

Sources & evidence

ORD record
ord-7e587eea4b59471d904a178159ecbb35
Source dataset
uspto-grants-2007_01
Patent number
US07160876B2

Reaction notes

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