Methanol → HCID 67421915, compound

HRID 658045Notes

Reaction equation

HRID 658045 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17](CCCN(C)C)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC3C=CC=CC=3)[CH:22]=2)=[O:19])=[CH:12][CH:11]=1.[C:42](OCC)(=O)[CH3:43].CO.[CH3:50][N:51]([CH:53]=O)[CH3:52]>[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:19])[CH2:42][CH2:43][CH2:53][N:51]([CH3:52])[CH3:50])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 58001010HCID 58001010, compound

Product 1

HCID 67421915HCID 67421915, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10% Palladium on carbon (100 mg) was added to a solution of N-(2-aminophenyl)-4-[3-(3-benzyloxyphenyl)-1-(3-dimethylaminopropyl)ureidomethyl]benzamide (Compound No. 1-76, 640 mg, 1.2 mmol) in a mixed solvent (ethyl acetate (10 mL), methanol (10 mL), and DMF (10 mL)), and then the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 32 hours. After the insoluble was filtered off, water (100 mL) was added to the filtrate, the whole was extracted with ethyl acetate (100 mL) twice, and then the organic layer was washed with brine (100 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 480 mg of the title compound as a white amorphous product. (Yield 88%)

Workup

  1. filtrationAfter the insoluble was filtered off
  2. additionwater (100 mL) was added to the filtrate
  3. extractionthe whole was extracted with ethyl acetate (100 mL) twice
  4. washthe organic layer was washed with brine (100 mL) twice
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b483e13342246ca826f518dd45b33f0
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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