Fumaric Acid → 4-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]aniline hemifumarate

HRID 969995Notes

Reaction equation

HRID 969995 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:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(OCC)(=O)C.C(O)C>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[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:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=3)=[CH:12][N:11]=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:15]=[CH:14][C:13]([C:16]3[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 111622684-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]aniline

Product 1

HCID 1317267214-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]aniline hemifumarate

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 18C (150 mg, 0.5 mmol) in ethyl acetate:ethanol (1:1, 5 mL) was treated with fumaric acid (58 mg, 0.5 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (178.2 mg, yield, 98%). 1H NMR (300 MHz, MeOH-d4) δ 1.74-2.11 (m, 3H), 2.20-2.36 (m, 1H), 2.44-2.53 (m, 1H), 3.13-3.40 (m, 5H), 3.68-3.79 (m, 1H), 5.27-5.35 (m, 1H), 6.68 (s, 1.2H), 6.81 (d, J=8.8 Hz, 2H), 7.37 (d, J=8.8 Hz, 2H), 8.74 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+. Anal. Calculated for C17H20N4O.0.57C4H4O4: C, 63.88; H, 6.19; N, 15.54. Found: C, 63.73; H, 6.21; N, 15.51.

Sources & evidence

ORD record
ord-78e6f486187f456184abcbeea592f76e
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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