Methanol → HCID 58508807, compound

HRID 454609Notes

Reaction equation

HRID 454609 reaction equation
CO.C([O:10][C:11]1[CH:38]=[C:37]([N:39]([CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[CH3:40])[CH:36]=[CH:35][C:12]=1[C:13]([NH:15][C:16]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:14])C1C=CC=CC=1>[C].[Pd].C(Cl)(Cl)Cl>[CH3:45][N:43]([CH3:44])[CH2:42][CH2:41][N:39]([CH3:40])[C:37]1[CH:36]=[CH:35][C:12]([C:13]([NH:15][C:16]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:25][C:17]=2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:14])=[C:11]([OH:10])[CH:38]=1

Participants

5

Reactant 2

HCID 887Methanol2×HCID 66990551HCID 66990551, compound

Product 1

HCID 58508807HCID 58508807, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a methanol (3.0 mL) solution of the obtained tert-butyl 2-(2-(benzyloxy)-4-((2-(dimethylamino)ethyl)(methyl)amino)benzamido)-4-phenylbenzoate (0.071 g), 10% palladium-carbon (0.035 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 45 minutes. Methanol (2.0 mL) and chloroform (1.0 mL) were added to the reaction mixture, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. The insoluble substance was removed by filtration, and then the solvent was evaporated under reduced pressure. Ethyl acetate was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.045 g of tert-butyl 2-(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-hydroxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hours
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. additionEthyl acetate was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-8d6ca2cae12b4816a28298dd20e8e9d9
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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