Sodium Hydroxide → 3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde

HRID 1243420Notes

Reaction equation

HRID 1243420 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[CH3:12])=[O:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.O>[CH3:12][C:4]1[C:5]([C:9]([N:53]2[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]2)=[O:11])=[C:6]([CH3:8])[NH:7][C:3]=1[CH:1]=[O:2]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 121115823,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1.67 g, 10 mmol) in dimethylformamide (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)- phosphonium hexafluorophosphate (BOP reagent, 6 g, 13.5 mmol) followed by 3 mL of diisopropylethylamine. After stirring for 5 minutes, 2 mL of 1-methylpiperazine was added and the mixture was stirred at room temperature for 24 hours. To the reaction was then added 25 mL of 1N sodium hydroxide and 25 mL of brine. After stirring for 30 minutes, the reaction mixture was poured into water (100 mL) and extracted (3×200 mL) with 10% of methanol in dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and evaporated on a rotary evaporator. The residue which remained was purified by chromatography(silica gel column, 5%-10% of methanol in dichloromethane) to give 1 g (40%) of 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carboxaldehyde.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. stirringAfter stirring for 30 minutes
  3. extractionextracted (3×200 mL) with 10% of methanol in dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated on a rotary evaporator
  6. customThe residue which remained was purified by chromatography(silica gel column, 5%-10% of methanol in dichloromethane)

Sources & evidence

ORD record
ord-ff8de3e6bc6b441fa2d6b8c3620daed7
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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