Fumaric Acid → N-{4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenyl}acetamide hemifumarate

HRID 969991Notes

Reaction equation

HRID 969991 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(OCC)(=O)C.C(O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2.[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11427728n-{4-[5-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenyl}acetamide

Product 1

HCID 131726720N-{4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenyl}acetamide hemifumarate

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 17A (50 mg, 0.15 mmol) in ethyl acetate/ethanol (3 mL, 1:1) was treated with fumaric acid (23 mg, 0.2 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (40 mg, yield, 63%). 1H NMR (MeOH-d4, 300 MHz) δ 1.77-2.17 (m, 6H), 2.21-2.37 (m, 1H), 2.47-2.56 (m, 1H), 3.13-3.40 (m, 5H), 3.71-3.83 (m, 1H), 5.31-5.38 (m, 1H), 6.68 (m, 1.2H), 7.68 (d, J=8.8 Hz, 2H), 7.92 (d, J=8.8 Hz, 2H), 8.31 (d, J=1.4 Hz, 1H), 8.59 (d, J=1.4 Hz, 1H) ppm. MS (DCl/NH3) m/z 339 (M+H)+. Anal. Calculated for C19H22N4O2.0.63C4H4O4.0.7H2O: C, 60.94; H, 6.16; N, 13.21. Found: C, 60.79; H, 6.18; N, 13.37.

Sources & evidence

ORD record
ord-e90b341b88604172bf2804fbf2d1df93
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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