Ethanol → HCID 69434838, compound

HRID 969984Notes

Reaction equation

HRID 969984 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:21]=[CH:20][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2.C(O)C.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(OCC)(=O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 702EthanolHCID 444972Fumaric AcidHCID 11222474N-[4'-(1-azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-yl]-N-phenylamine

Product 1

HCID 69434838HCID 69434838, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 11A (200 mg, 0.54 mmol) in ethyl acetate:ethanol (5 mL, 1:1) was treated with fumaric acid (70 mg, 0.6 mmol). The title compound was obtained as a solid (197.8 mg, yield, 72%). 1H NMR (MeOH-d4, 300 MHz) δ 1.81-2.20 (m, 3H), 2.27-2.42 (m, 1H), 2.50-2.58 (m, 1H), 3.17-3.48 (m, 5H), 3.75-3.87 (m, 1H), 4.85-4.93 (m, 1H), 6.71 (s, 2.5H), 6.81-6.89 (m, 1H), 7.02 (d, J=8.8 Hz, 2H), 7.07-7.17 (m, 4H), 7.18-7.27 (m, 2H), 7.45 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 371 (M+H)+. Anal. Calculated for C25H26N2O.1.2C4H4O4: C, 70.21; H, 6.09; N, 5.50. Found: C, 70.09; H, 6.17; N, 5.43.

Sources & evidence

ORD record
ord-3510d5fbfa4d4675a33f9e120cfdb57b
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

Loading…