Sodium Methoxide → HCID 25121190, compound

HRID 2280954Notes

Reaction equation

HRID 2280954 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-c73a53cb5d46416cb0767b5b436644b0
Source dataset
uspto-grants-2015_09
Patent number
US09139559B2

Reaction notes

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