Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86606874, compound

HRID 749416Notes

Reaction equation

HRID 749416 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[C:9]([C:11]1[CH:12]=[C:13]([C:21]([N:23]([CH2:25][C@H:26]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([Cl:50])[CH:44]=2)[CH2:27][CH2:28][N:29]2[CH2:32][CH:31]([N:33]3[CH2:42][CH2:41][C:36]4([O:40]CC[O:37]4)[CH2:35][CH2:34]3)[CH2:30]2)[CH3:24])=[O:22])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)#[N:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:10].[C:5]([OH:8])(=[O:7])[CH3:6].[C:36]([OH:40])(=[O:37])[CH3:35].[C:9]([C:11]1[CH:12]=[C:13]([C:21]([N:23]([CH2:25][C@H:26]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([Cl:50])[CH:44]=2)[CH2:27][CH2:28][N:29]2[CH2:32][CH:31]([N:33]3[CH2:34][CH2:35][C:36](=[O:37])[CH2:41][CH2:42]3)[CH2:30]2)[CH3:24])=[O:22])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)#[N:10]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86606875HCID 86606875, compound

Product 2

HCID 517165Ammonium AcetateHCID 86606874HCID 86606874, compoundYield 176.5%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Catalyst

Procedure

3-cyano-N-{(2S)-2-(3,4-dichlorophenyl)-4-[3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)azetidin-1-yl]butyl}-N-methyl-1-naphthamide diacetate (see Example 25; 35 mg, 0.058 mmol) was dissolved in a few drops of acetone-water (1:1) and to the resultant solution was added pyridinium p-toluenesulfonate (43 mg, 0.17 mmol). The mixture was subjected to microwave single node heating for 10 min and then the solvent was removed by evaporation. The residue was dissolved in CH2Cl2 and the solution was washed with NaHCO3 aq. then dried over MgSO4. Removal of solvent by evaporation yielded an oil, which was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 35 mg (89%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): 1.4-2.2 (cm, 3H), 1.9 (s, 6H), 2.3-4.0 (cm, 20H), 6.4-7.8 (cm, 7H), 8.0-8.2 (cm, 1H), 8.6 (d, 1H); LCMS: m/z 563 (M+1)+.

Workup

  1. temperatureheating for 10 min
  2. customthe solvent was removed by evaporation
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe solution was washed with NaHCO3 aq.
  5. dry with materialthen dried over MgSO4
  6. customRemoval of solvent
  7. customby evaporation
  8. customyielded an oil, which
  9. customwas purified by reversed phase chromatography
  10. additiona mixture of acetonitrile

Sources & evidence

ORD record
ord-1ee1bd7e41b34194aacb031b977963d4
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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