Sodium Methoxide → HCID 25121190, compound

HRID 2359528Notes

Reaction equation

HRID 2359528 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:27])[C:15](=[O:26])[CH2:16][NH:17][C:18]2[C:23](Cl)=[CH:22][N:21]=[N:20][C:19]=2[Cl:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][O-:29].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:27])[C:15](=[O:26])[CH2:16][NH:17][C:18]2[C:23]([O:29][CH3:28])=[CH:22][N:21]=[N:20][C:19]=2[Cl:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59336185HCID 59336185, compound

Product 1

HCID 25121190HCID 25121190, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Compound 139 (10 mg) and sodium methoxide (1.3 mg) in methanol (1 mL) was stirred overnight under reflux. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.,; NH-DM1020) column chromatography (ethyl acetate: hexane=1:9 to 1:1) to give 3.0 mg (30% yield) of the desired product as a white amorphous.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.,; NH-DM1020) column chromatography (ethyl acetate: hexane=1:9 to 1:1)

Sources & evidence

ORD record
ord-0ef2886de29342bc8ac4894b5e22d951
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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