Fumaric Acid → 5-[2-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline Fumarate

HRID 970005Notes

Reaction equation

HRID 970005 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:23])=[C:20]([CH:22]=3)[NH2:21])=[CH:12][N:11]=1)[CH2:2]2.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]>C(OCC)(=O)C.C(O)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:23])=[C:20]([CH:22]=3)[NH2:21])=[CH:12][N:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 112553565-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline

Product 1

HCID 694382345-[2-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline Fumarate

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 23A (45 mg, 0.14 mmol) in ethyl acetate/ethanol (1:1, 3 mL) was treated with fumaric acid (23 mg, 0.2 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (50 mg, yield, 78%). 1H NMR (300 MHz, MeOH-d4) δ 1.85-2.24 (m, 6H), 2.30-2.44 (m, 1H), 2.55-2.62 (m, 1H), 3.23-3.46 (m, 5H), 3.82-3.92 (m, 1H), 5.36-5.44 (m, 1H), 6.69 (s, 2H), 6.87 (dd, J=2.0, 7.8 Hz, 1H), 6.96 (d, J=1.7 Hz, 1H), 7.12 (d, J=8.1 Hz, 1H), 8.78 (s, 2H). ppm. MS (DCl/NH3) m/z 311 (M+H)+. Anal. Calculated for C18H22N4O.1.15C4H4O4: C, 61.15; H, 6.04; N, 12.62. Found: C, 61.14; H, 6.08; N, 12.38.

Sources & evidence

ORD record
ord-c250ce8d43f94850b8a24d79e048aaac
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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