Hydrogen Peroxide → HCID 86606873, compound

HRID 749414Notes

Reaction equation

HRID 749414 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([C:7]1[CH:8]=[C:9]([C:17]([N:19]([CH2:21][C@H:22]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=2)[CH2:23][CH2:24][N:25]2[CH2:28][CH:27]([N:29]3[CH2:34][CH2:33][S:32][CH2:31][CH2:30]3)[CH2:26]2)[CH3:20])=[O:18])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)#[N:6].OO>C(O)(=O)C.O>[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:6].[C:1]([OH:4])(=[O:3])[CH3:2].[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([C:7]1[CH:8]=[C:9]([C:17]([N:19]([CH2:21][C@H:22]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=2)[CH2:23][CH2:24][N:25]2[CH2:28][CH:27]([N:29]3[CH2:34][CH2:33][S:32](=[O:3])[CH2:31][CH2:30]3)[CH2:26]2)[CH3:20])=[O:18])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)#[N:6]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 68978898HCID 68978898, compound

Product 2

HCID 517165Ammonium AcetateHCID 86606873HCID 86606873, compoundYield 147.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-N-methyl-1-naphthamide acetate (see Example 24; 127 mg, 0.20 mmol) was dissolved in acetic acid (10 mL) and to the resultant solution was added hydrogen peroxide (0.04 mL of 30% aqueous solution, 0.35 mmol). The mixture was stirred at room temperature for 3 days then diluted with water. The solvent was removed by lyophilising the mixture to give a residue, which was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 52 mg (35%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): 1.2-2.2 (m, 3H), 1.9 (s, 3H), 2.3-3.6 (m, 20H), 4.4 (c m, 1H), 6.4-7.6 (m, 2H), 7.4 (dd, 1H), 7.6-8.2 (5H), 8.6 (d, 1H); LCMS: m/z 583 (M+1)+.

Workup

  1. customThe solvent was removed
  2. customto give a residue, which
  3. customwas purified by reversed phase chromatography
  4. additiona mixture of acetonitrile

Sources & evidence

ORD record
ord-cbee4a48c81d4539b0075b7a7ebf035a
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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