Sodium Hydroxide → HCID 54380946, compound

HRID 1937533Notes

Reaction equation

HRID 1937533 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]([CH3:54])[CH2:51][CH2:52][NH2:53].[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.O>[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52][NH:53][C:9]([C:5]1[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[CH3:8])=[O:11]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 54380946HCID 54380946, compoundYield 42%

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 dimethylforamide (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent, 6 g, 13.5 mmol) followed by 3 mL diisopropylethylamine. After stirring for 5 minutes, 1 mL of N,N-dimethylethylendiamine was added and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added 25 mL of 1 N 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 using a rotary evaporator. The residue which remained was purified by chromatography (silica gel column, 5%-10% methanol in dichloromethane) to give 1 g (42%) of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-dimethylamino-ethyl)-amide.

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
  6. customa rotary evaporator
  7. customThe residue which remained was purified by chromatography (silica gel column, 5%-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1dbe62a0406e4c0ca7335ab630b42356
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

Loading…