HCID 67523892, compound → HCID 24998583, compound

HRID 659037Notes

Reaction equation

HRID 659037 reaction equation
C1(OC([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])[N:31]=5)=[CH:25][CH:24]=4)=[O:21])[CH:17]=3)[C:12]([CH3:42])([CH3:41])[CH2:11]2)=O)C=CC=CC=1>[Pd].C1COCC1>[CH3:41][C:12]1([CH3:42])[C:13]2[C:18](=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])[N:31]=4)=[CH:27][CH:28]=3)=[O:21])=[CH:15][CH:14]=2)[NH:10][CH2:11]1

Participants

4

Reactant 1

HCID 67523892HCID 67523892, compound

Product 1

HCID 24998583HCID 24998583, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 540 mg (927 mmol) 6-(3-{4-[2-(3-Hydroxy-propylamino)-pyrimidin-4-yloxy]-phenyl}-ureido)-3,3-dimethyl-2,3-dihydro-indole-1-carboxylic acid phenyl ester, 20 ml THF and 150 mg 10% Pd/C is hydrogenated at atmospheric pressure for 10 h. The catalyst is removed by filtration and the filtrate evaporated. The residue is purified by chromatography on silica (dichloromethane/methanol 95:5) and the obtained material (400 mg) stirred with dichloromethane for 1 h. the precipitate is isolated by filtration and washed with dichloromethane to give 150 mg (36%) of the title compound.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue is purified by chromatography on silica (dichloromethane/methanol 95:5)
  4. customis isolated by filtration
  5. washwashed with dichloromethane

Sources & evidence

ORD record
ord-a3d9a27bc9714fb8bffb2acf905526ab
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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