HCID 86591270, compound → HCID 10202081, compound

HRID 584979Notes

Reaction equation

HRID 584979 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.[H][H]>CO.O1CCOCC1.[Pd]>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([NH:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:23])[CH:16]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

5

Reactant 2

HCID 86591270HCID 86591270, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10202081HCID 10202081, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
50 °C

Procedure

460 mg (1.1 mmol) of 1-[4′-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-yl]-3-phenylurea in 20 ml of a methanol/dioxane mixture (1/1) are placed in a reactor. The reaction medium is degassed and 560 mg (1.2 equivalents by mass) of 10% palladium-on-charcoal are then added. The system is placed under 3 bar of hydrogen and heated at 50° C. for hours. The reaction medium is filtered through Celite and evaporated, and the residue obtained is purified by chromatography on a column of silica with a gradual increase in the polarity of a 9/1 mixture of heptane and ethyl acetate to a 4/6 mixture of heptane and ethylacetate. After evaporation of the solvents, 150 mg (33%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-phenylurea are obtained in the form of a white solid with a melting point of 185° C.

Workup

  1. customThe reaction medium is degassed
  2. filtrationThe reaction medium is filtered through Celite
  3. customevaporated
  4. customthe residue obtained
  5. customis purified by chromatography on a column of silica with
  6. temperaturea gradual increase in the polarity of a 9/1 mixture of heptane and ethyl acetate to a 4/6 mixture of heptane and ethylacetate
  7. customAfter evaporation of the solvents, 150 mg (33%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-phenylurea
  8. customare obtained in the form of a white solid with a melting point of 185° C.

Sources & evidence

ORD record
ord-8836e5eb32624741846d10e314d4a201
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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