Ethyl Acetate → HCID 59224885, compound

HRID 905652Notes

Reaction equation

HRID 905652 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC=CC=3)=[CH:24][CH:23]=2)=[O:20])=[CH:13][N:12]=1)=[O:10].C(OCC)(=O)C>[Pd].CO>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[O:20])=[CH:13][N:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59225037HCID 59225037, compound

Product 1

HCID 59224885HCID 59224885, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 10% palladium on carbon (30 mg) was added to a solution of N-(2-aminophenyl)-5-[3-(4-benzyloxyphenyl)-1-[5-(morpholin-4-yl)pentyl]ureidomethyl]pyridine-2-carboxylic acid amide (Compound No. 1-182, 45 mg, 0.072 mmol) in a mixed solvent (ethyl acetate (2.0 mL) and methanol (3.0 mL)), and then the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours. After the insoluble was filtered off with celite, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 32 mg of the title compound as a yellow oil. (Yield 84%)

Workup

  1. filtrationAfter the insoluble was filtered off with celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-163c38821635433b9750c3d7472e2fc3
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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