HCID 18626983, compound → HCID 178489154, compound

HRID 1860264Notes

Reaction equation

HRID 1860264 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.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:25]([CH:26]=O)=[CH:24][NH:23][N:22]=2)=[CH:17][CH:16]=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:26]/[C:25]1[C:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[N:22][NH:23][CH:24]=1

Participants

5

Reactant 2

HCID 18626983HCID 18626983, compoundHCID 178489158HCID 178489158, compound

Product 1

HCID 178489154HCID 178489154, compoundYield 52.6%

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 (25 mg, 0.14 mmol) was dissolved in a solution of 1% piperidine in 2-propanol (2 ml). 3-(4-Methoxyphenyl)-1H-pyrazole-4-carboxaldehyde (0.15 mmol, 28 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 27 mg of (Z)-5,6-dihydro-5-oxo-4-[[3-(4-methoxyphenyl)-1H-pyrazol-4-yl]methylene]-4H-thieno [2,3-b]pyrrole-2-carboxamide as a brown solid. MS(ES): m/e 367 [M+H].

Workup

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

Sources & evidence

ORD record
ord-b996e37b0a9f41ec9af521d487465aba
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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