Hydrogen Peroxide → HCID 59729935, compound

HRID 228247Notes

Reaction equation

HRID 228247 reaction equation
[CH3:1][C:2]1[CH:16]=[C:15]([CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][CH:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1.C(=O)([O-])[O-:32].[K+].[K+].OO.CO>CS(C)=O>[CH3:1][C:2]1[CH:16]=[C:15]([CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][CH:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]([NH2:10])=[O:32])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 11430Potassium CarbonateHCID 59730055(+/-)-6-[2-Methyl-4-(4-phenyl-azepan-1ylmethyl)-phenoxy]-nicotinonitrile

Product 1

HCID 59729935HCID 59729935, compoundYield 173.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using a method similar to Example 371, (±)-6-[2-methyl-4-(4-phenyl-azepan-1ylmethyl)-phenoxy]-nicotinonitrile (compound of example 368) (0.246 g, 0.642 mmol), potassium carbonate (0.0429 g, 0.310 mmol), and 30% hydrogen peroxide Solution (aq) (0.220 mL, 1.94 mmol) in dimethylsulfoxide provide, after ion exchange chromatography (methanol→2 M ammonia/methanol), 0.223 g (87%) of the title compound as a while solid: high resolution mass spectrum (electrospray): m/z calc for C25H25N3O2 402.2182, found 402.2172; 1H NMR (methanol-d4): 8.67 (d, 1H, J=2.0 Hz), 8.36 (dd, 1H, J=2.4, 8.8 Hz), 7.51 (d, 2H, J=8.3 Hz), 7.32-7.22 (m, 4H), 7.20-7.14 (m, 3H), 7.04 (d, 1H, J=8.8 Hz), 3.77 (s, 2H), 2.97 (ddd, 1H, J=3.4, 6.3, 13.2 Hz), 2.92-2.83 (m, 3H), 2.81-2.72 (m, 1H), 2.04-1.76 (m, 6H).

Workup

  1. customprovide

Sources & evidence

ORD record
ord-e0b6d60c547d4955a5d1bc28d97c1f18
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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