HCID 18626983, compound → HCID 178513499, compound

HRID 1860263Notes

Reaction equation

HRID 1860263 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([NH2:12])=[O:11])=[CH:9][C:4]=2[CH2:3]1.[C:13]1([C:19]2[C:23]([CH:24]=O)=[CH:22][NH:21][N:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1CCCCC1.CC(O)C>[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([NH2:12])=[O:11])=[CH:9][C:4]=2/[C:3]/1=[CH:24]/[C:23]1[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:20][NH:21][CH:22]=1

Participants

5

Reactant 2

HCID 18626983HCID 18626983, compoundHCID 178519874HCID 178519874, compound

Product 1

HCID 178513499HCID 178513499, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
75 °C

Procedure

5,6-Dihydro-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxamide (30 mg, 0.17 mmol) was dissolved in a solution of 1% piperidine in 2-propanol (2 ml). 3-Phenyl-1H-pyrazole-4-carboxaldehyde (0.18 mmol, 31 mg) was added in one portion and the mixture heated at 75° C. for 1 hour. The reaction mixture was poured into an ice/water mixture (2 ml) and the precipitated solid was collected by filtration and washed with water to give 26 mg of (Z)-5,6-dihydro-5-oxo-4-[(3-phenyl-1H-pyrazol-4-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxamide as a yellow/brown solid. MS(ES): m/e 337 [M+H].

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-d19dda4e2fd2405585c0f1cba46562e4
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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