Piperidine → HCID 69844752, compound

HRID 1860261Notes

Reaction equation

HRID 1860261 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.N1C=CC=C1[CH:18]=[O:19].[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CC(O)C>[CH3:18][O:19][C:23]1[CH:22]=[CH:21][NH:20][C:25]=1/[CH:24]=[C:3]1/[C:4]2[CH:9]=[C:8]([C:10]([NH2:12])=[O:11])[S:7][C:5]=2[NH:6][C:2]/1=[O:1]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 13854Pyrrole-2-carboxaldehydeHCID 18626983HCID 18626983, compound

Product 1

HCID 69844752HCID 69844752, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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). Pyrrole-2-carboxaldehyde (0.19 mmol, 23 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 22 mg of (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxamide as a red/brown solid. MS(ES): m/e 247 [M+H].

Workup

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

Sources & evidence

ORD record
ord-d6741925ce6949508737c74b0a51af0a
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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