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

HRID 969998Notes

Reaction equation

HRID 969998 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H: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)[C@@H: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)[C@@H: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 112201784-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}aniline

Product 1

HCID 1317267224-{2-[(3R)-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 19C (30 mg, 0.1 mmol) in ethyl acetate/ethanol (1:1, 2 mL) was treated with fumaric acid (12 mg, 0.1 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (13.6 mg, yield, 35%). 1H NMR (300 MHz, MeOH-d4) δ 1.84-2.20 (m, 3H), 2.28-2.44 (m, 1H), 2.53-2.62 (m, 1H), 3.16-3.45 (m, 5H), 3.81-3.91 (m, 1H), 5.34-5.42 (m, 1H), 6.68 (s, 1.5H), 6.81 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 8.75 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+. Anal. Calculated for C17H20N4O.0.7C4H4O4O.0.45H2O: C, 61.65; H, 6.19; N, 14.52. Found: C, 61.41; H, 6.02; N, 14.80.

Sources & evidence

ORD record
ord-9be9ab05f6d249f18d3c3f61a6f83e2e
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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