Sodium Bicarbonate → 2-[(Aminocarbonyl)amino]-5-[4-formylphenyl]thiophene-3-carboxamide

HRID 1675528Notes

Reaction equation

HRID 1675528 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[NH2:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=1.[CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])O.[Na+]>COCCOC>[C:8]([NH:7][C:5]1[S:6][C:2]([C:19]2[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=2)=[CH:3][C:4]=1[C:11]([NH2:13])=[O:12])(=[O:10])[NH2:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5910734-Formylphenylboronic AcidHCID 111846265-Bromo-2-ureidothiophene-3-carboxamide

Product 1

HCID 219143262-[(Aminocarbonyl)amino]-5-[4-formylphenyl]thiophene-3-carboxamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 5-bromo-2-(carbamoylamino)thiophene-3-carboxamide (1.0 g, 3.79 mmol), 4-formylphenylboronic acid (0.625 g, 4.17 mmol) and tetrakis(triphenylphosphine) Pd catalyst (0.438 g, 0.379 mmol) in DME (50 ml) was added a saturated aqueous solution of sodium hydrogen carbonate (10 ml). The reaction vessel was flushed with nitrogen and heated to 90° C. overnight. LCMS indicated complete consumption of the starting material. The reaction mixture was concentrated using a rotary evaporator. The resultant dark brown residue was dissolved in DCM (17 ml) and stirred with aqueous 2M sodium hydroxide solution (8.5 ml) for 20 minutes. Diethyl ether (20 ml) was added and the mixture stirred for a further 30 minutes. The resultant suspension was sonicated for 2 minutes. Filtration gave a precipitate, which was washed with hot diethyl ether to give a coloured solid (440 mg).

Workup

  1. customThe reaction vessel was flushed with nitrogen
  2. customconsumption of the starting material
  3. concentrationThe reaction mixture was concentrated
  4. customa rotary evaporator
  5. dissolutionThe resultant dark brown residue was dissolved in DCM (17 ml)
  6. additionDiethyl ether (20 ml) was added
  7. stirringthe mixture stirred for a further 30 minutes
  8. customThe resultant suspension was sonicated for 2 minutes
  9. filtrationFiltration
  10. customgave a precipitate, which
  11. washwas washed with hot diethyl ether

Sources & evidence

ORD record
ord-4b929895b2734de9a3618c0cda8344e7
Source dataset
uspto-grants-2011_08
Patent number
US08003695B2

Reaction notes

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