Fumaric Acid → HCID 21072612, compound

HRID 1372843Notes

Reaction equation

HRID 1372843 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[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]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:11]=[CH:12][C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 117715294-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole

Product 1

HCID 21072612HCID 21072612, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 2B (48 mg, 0.15 mmol) was treated with fumaric acid (23 mg, 0.2 mmol) in EtOAc/EtOH (v. 1:1, 3 mL) at ambient temperature for 15 h. The title compound was obtained as solid (60.2 mg, yield, 90%). 1H NMR (300 MHz, CD3OD) δ 1.82–2.19 (m, 3H), 2.29–2.42 (m, 1H), 2.51–2.58 (m, 1H), 3.16–3.46 (m, 5H), 3.75–3.85 (m, 1H), 4.89–4.96 (m, 1H), 6.56 (dd, J=3.4, 1.0 Hz, 1H), 6.69 (s, 2.2H), 7.02 (dd, J=7.1, 1.0 Hz, 1H), 7.08 (dt, J=8.8, 2.5 Hz, 2H), 7.15 (t, J=7.5 Hz, 1H), 7.26 (d, J=3.4 Hz, 1H), 7.35 (dt, J=8.1, 1.0 Hz, 1H), 7.64 (dt, J=8.8, 2.6 Hz, 2H) ppm. MS (DCl/NH3): m/z 319 (M+H)+. Anal. Calculated for C21H22N2O.1.12C4H4O4: C, 68.25; H, 5.95; N, 6.25. Found: C, 68.43; H, 5.58; N, 6.20.

Sources & evidence

ORD record
ord-a0c957cfe6844acab377aaaa6199c607
Source dataset
uspto-grants-2007_01
Patent number
US07160876B2

Reaction notes

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