Sodium hydride → HCID 89498656, compound

HRID 1430285Notes

Reaction equation

HRID 1430285 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]=1[CH3:7].[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN(C)C(=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:16][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 89498475HCID 89498475, compound

Product 1

HCID 89498656HCID 89498656, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of EXAMPLE 151B (356 mg) in N,N-dimethylacetamide (6 mL) was added NaH (128 mg, 60% in mineral oil). The mixture was stirred for 30 minutes. Then, 1-bromo-2-methoxyethane (740 mg) was added to the mixture, which was stirred overnight. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with water, brine and dried over Na2SO4. After filtration and concentration, the residue containing the crude title compound was used in the next reaction without further purification.

Workup

  1. stirringwas stirred overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. additionthe residue containing the crude title compound
  6. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-36cd76b1de6543a397d42e9893376979
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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