Water → 5-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid Amide

HRID 2223361Notes

Reaction equation

HRID 2223361 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=1.C(N(CC)CC)C.[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C.[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:21]1([C:27]#[C:28][C:2]2[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 111846265-Bromo-2-ureidothiophene-3-carboxamide

Product 1

HCID 100167795-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid AmideYield 18%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-ureido-thiophene-3-carboxylic acid amide (0.264 g, 1.0 mmol), copper (I) iodide (0.005 g), triphenyl phosphene (0.030 g, 15 mole %), palladium acetate (0.010 g, 5% mole %), triethyl amine (1 mL) and phenylacetylene (0.1 g, 1.1 mmol) in DMF (4 mL) was added to a 9 mL reaction vial. The reaction vial was sealed and heated to 100° C. in a Smith Microwave Synthesizer for 20 min. Water (5 mL) and ethyl acetate (20 mL) were added to the reaction mixture, the organic phase was separated and then washed with brine (2×10 mL) and water (1×10 mL), and dried over anhydrous magneium sulfate. After filtration, the solvent was removed under vacuum and the crude residue was taken into DMSO (5 mL) and purified utilizing a Gilson preparative HPLC to give the above titled compound as a light brown solid (0.050 g, 0.18 mmol, 18% yield). LC-MS [M+H]+ m/z 286.

Workup

  1. customThe reaction
  2. customvial was sealed
  3. customthe organic phase was separated
  4. washwashed with brine (2×10 mL) and water (1×10 mL)
  5. dry with materialdried over anhydrous magneium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum
  8. custompurified

Sources & evidence

ORD record
ord-44a9e0d2b5184a4e92ecfc07f334e9f8
Source dataset
uspto-grants-2008_05
Patent number
US07375131B2

Reaction notes

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