HCID 22177839, compound → HCID 10110219, compound

HRID 1157528Notes

Reaction equation

HRID 1157528 reaction equation
[CH3:1][CH2:2][CH:3]([NH:6][C:7]1[N:12]2[N:13]=[C:14]([CH3:25])[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[CH3:24])=[C:11]2[N:10]=[C:9]2[CH2:26][CH2:27][O:28][C:8]=12)[CH2:4][CH3:5]>C1(OC2C=CC=CC=2)C=CC=CC=1.CO.[C].[Pd]>[CH3:1][CH2:2][CH:3]([NH:6][C:7]1[N:12]2[N:13]=[C:14]([CH3:25])[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[CH3:24])=[C:11]2[N:10]=[C:9]2[CH:26]=[CH:27][O:28][C:8]=12)[CH2:4][CH3:5]

Participants

5

Reactant 1

HCID 22177839HCID 22177839, compound

Product 1

HCID 10110219HCID 10110219, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

To a solution of the compound prepared in Example 2(6) (215 mg) in diphenyl ether (3 ml), 10% palladium carbon (150 mg) was added, and the mixture was stirred for 4 hours at 250° C. After the reaction mixture was cooled to room temperature, it was diluted with methanol (10 ml). The diluted solution was filtered though celite (registered trademark). The filtrate was concentrated, and the residue was purified by column chromatography on silica gel (n-hexane:acetone=9:1) to give the title compound (150 mg) having the following physical data.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe diluted solution was filtered though celite (registered trademark)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (n-hexane:acetone=9:1)

Sources & evidence

ORD record
ord-89610c9ddf8b4b9e9565c153939c5d1b
Source dataset
uspto-grants-2010_10
Patent number
US07807688B2

Reaction notes

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