Sodium hydride → HCID 67144758, compound

HRID 2273737Notes

Reaction equation

HRID 2273737 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl.[CH3:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:36][CH2:35][N:33]([CH3:34])[CH3:32])[C:9]=2[CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×HCID 67144515HCID 67144515, compound

Product 1

HCID 67144758HCID 67144758, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EXAMPLE 199A (1.5 g) in N,N-dimethylformamide (20 ml) was added 60% sodium hydride (0.596 g). The mixture was stirred at room temperature for 30 minutes and dimethylaminoethyl chloride hydrochloride salt (1.073 g) was added. After the resulting mixture was stirred overnight, additional 60% sodium hydride (0.596 g) and dimethylaminoethyl chloride hydrochloride salt (1.073 g) were added. The reaction mixture was further stirred overnight, diluted with ethyl acetate and washed with water, saturated NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to provide the title compound.

Workup

  1. stirringAfter the resulting mixture was stirred overnight
  2. waitThe reaction mixture was further stirred overnight
  3. washwashed with water, saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5730cb32bd394144b5177ea2980710d5
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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