Water → HCID 68458152, compound

HRID 2358660Notes

Reaction equation

HRID 2358660 reaction equation
C(OC(=O)[N:7]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[OH:26])[C:8]1[C:17]2[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)(C)(C)C.Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:34][CH:35]=2)=[C:19]([NH:7][C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 148705Acetamide, N-(4-(chloromethyl)phenyl)-HCID 68456168HCID 68456168, compound

Product 1

HCID 68458152HCID 68458152, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Example 104B (37 mg, 0.1 mmol), N-(4-chloromethyl-phenyl)-acetamide (22 mg, 0.12 mmol), cesium carbonate (130 mg, 0.4 mmol) and tetrabutylammonium iodide (0.001 g) in DMF (1 ml) was stirred at room temperature for 16 hours. The mixture was poured into water and extracted by ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was added dichloromethane (2 mL) and trifluoroacetic acid (2 mL) and stirred at room temperature for 2 hours. The solvent was evaporated and the crude residue was purified by chromatography on silica eluting with 2% methanol in dichloromethane to 5% methanol in dichloromethane to give the title compound as a trifluoroacetic acid salt (11 mg, 21%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.00 (s, 3 H) 2.31 (s, 3 H) 2.74 (s, 3 H) 5.05 (s, 2 H) 6.36 (d, J=6.99 Hz, 1 H) 7.12 (d, J=8.46 Hz, 2 H) 7.25 (m, 3 H) 7.40 (d, J=8.46 Hz, 2 H) 7.73 (d, J=8.46 Hz, 1 H) 8.43 (d, J=6.99 Hz, 1 H) 8.98 (d, J=8.46 Hz, 1 H) 9.89 (s, 1 H) 10.65 (s, 1 H) 14.25 (s, 1 H); MS (ESI+) m/z 413 (M+H)+.

Workup

  1. extractionextracted by ethyl acetate
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a2cce9fbb994d669555295a00cfe3f7
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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