Fumaric Acid → 2-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole Fumarate

HRID 1441402Notes

Reaction equation

HRID 1441402 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[NH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH: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:15]=[CH:14][C:13]([C:16]3[NH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][CH:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 114839822-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole

Product 1

HCID 210726022-[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 6C (70 mg, 0.22 mmol) was treated with fumaric acid (29 mg, 0.25 mmol) in EtOAc/EtOH (v. 1′:1, 3 mL) at ambient temperature for 10 h. The title compound was obtained as solid (87 mg, yield, 89%). 1H NMR (300 MHz, CD3OD) δ 1.81-2.18 (m, 3H), 2.25-2.39 (m, 1H), 2.48-2.56 (m, 1H), 3.19-3.48 (m, 5H), 3.73-3.85 (m, 1H), 4.86-4.93 (m, 1H), 6.65-6.80 (m, 2H), 6.94-7.10 (m, 4H), 7.36 (dd, J=8.1, 0.7 Hz, 1H), 7.49 (dt, J=7.8, 1.0 Hz, 1H), 7.75 (dt, J=9.2, 2.4 Hz, 2H) ppm. MS (DCI/NH3): m/z 319 (M+H)+. Anal. Calculated for C21H22N2.1.1 C4H4O4: C, 68.39; H, 5.96; N, 6.28. Found: C, 68.10; H, 6.22; N, 6.25.

Sources & evidence

ORD record
ord-007c87ad100a41d4aee561582eca39ec
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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