Sodium hydride → HCID 73848368, compound

HRID 1737210Notes

Reaction equation

HRID 1737210 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11](=[N:13][OH:14])[CH3:12].[H-].[Na+].[Cl:17][C:18]1[N:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31]Cl)[C:20](=[O:24])[N:21]([CH3:23])[N:22]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:17][C:18]1[N:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][O:14][N:13]=[C:11]([C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[CH:1]=2)[CH3:12])[C:20](=[O:24])[N:21]([CH3:23])[N:22]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 240448HCID 240448, compoundHCID 10956231HCID 10956231, compound

Product 1

HCID 73848368HCID 73848368, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the title compound of Step C (700 mg, 3.7 mmol) in dimethylformamide (10 mL) was added sodium hydride as a 60% oil dispersion (160 mg) followed by the title compound of Step B. The mixture was stirred at room temperature for 4 h and then was diluted with ethyl acetate. The solution was washed with water and then saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford an oil. Chromatography of this oil on silica gel with 20-30% ethyl acetate in hexanes afforded 1.0 g of the title compound of Step D, a compound of the invention, as an oil which solidified on standing. 1H NMR (CDCl3): δ 7.68 (m,7H), 5.2 (m,2H), 3.47 (s,3H), 2.75 (m,4H), 2.15 (s,3H), 1.78 (m,4H). This material was used in the preparation of Example 4 without further characterization.

Workup

  1. washThe solution was washed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford an oil

Sources & evidence

ORD record
ord-1db286a674804a7498f6b482b84c4373
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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