Triethylamine → HCID 22390974, compound

HRID 1372407Notes

Reaction equation

HRID 1372407 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1C)=[O:2].Cl.CN(C)CCCN=C=N.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>CN(C)C=O.C(=O)(O)[O-].[Na+].[OH-].[Na+].[Cl-].[Na+].O.[Cl-].[Na+]>[CH3:39][N:40]1[CH2:45][CH2:44][N:43]([C:8]([C:6]2[NH:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)=[O:10])[CH2:42][CH2:41]1

Participants

11

Reactant 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 98988845-formyl-4-methyl-1H-pyrrole-2-carboxylic AcidHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Product 1

HCID 22390974HCID 22390974, compound

Reagents, catalysts & solvents 5

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-Formyl-4-methyl-1H-pyrrole-2-carboxylic acid was dissolved in dimethylformamide (0.3M) with stirring. To this was added 1-ethyl-3-(3-dimethylamino-propylcarbodiimide hydrochloride (1.2 equivalents), 1-hydroxybenzotriazole (1.2 equivalents) followed by triethylamine (2 equivalents) and 1-methylpiperazine (1 equivalent) and the reaction stirred for 12 hours (General Amidation Procedure 1). The reaction was diluted with saturated sodium bicarbonate solution, sodium hydroxide solution, brine, solid sodium chloride and extracted twice with 10% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated. The resulting oil was re-concentrated from toluene and precipitated from diethyl ether:hexanes to afford 5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde as a solid. MS m/z 222 [M+1].

Workup

  1. stirringthe reaction stirred for 12 hours (General Amidation Procedure 1)
  2. extractionextracted twice with 10% methanol in dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. concentrationThe resulting oil was re-concentrated from toluene
  7. customprecipitated from diethyl ether

Sources & evidence

ORD record
ord-392b54b2906d4ae5a16ca98ce2516663
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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