HCID 22013033, compound → HCID 22012969, compound

HRID 378724Notes

Reaction equation

HRID 378724 reaction equation
[CH2:1]([O:3][CH:4]([O:40][CH2:41][CH3:42])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)=[O:30])([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:39])[CH3:2]>C(O)C.[Pd]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16](=[O:17])[NH:15][C:8]2([CH2:28][C:29]([NH:31][C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[O:30])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:6]([CH2:5][CH:4]([O:40][CH2:41][CH3:42])[O:3][CH2:1][CH3:2])[C:7]2=[O:39])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 22013033HCID 22013033, compound

Product 1

HCID 22012969HCID 22012969, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.62 g of (RS)-1-(2,2-diethoxyethyl)-3-((4-methylphenyl)aminocarbonylmethyl)-3-(N'-(4-nitrophenyl)ureido)indolin-2-one and 20 mg of 5% Pd/C in 100 ml of ethanol was stirred at room temperature for 12 hours under a hydrogen atmosphere. The reaction mixture was filtered through Cerite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 0.33 g (57%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Cerite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-00101c6c909944a3b2fadf0e5644ef2f
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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