Sodium Hydroxide → 5-Formyl-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid (3-diethylamino-2-hydroxy-propyl)-amide

HRID 349886Notes

Reaction equation

HRID 349886 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:2].[NH2:18][CH2:19][CH:20]([OH:27])[CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24].C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:23]([N:22]([CH2:25][CH3:26])[CH2:21][CH:20]([OH:27])[CH2:19][NH:18][C:9]([C:5]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[CH3:8])=[O:11])[CH3:24]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 516892Sodium BicarbonateHCID 219156195-Formyl-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 206047855-Formyl-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid (3-diethylamino-2-hydroxy-propyl)-amideYield 25.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-Formyl-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid (1.0 gm, 4.36 mmol), 1-amino-3-diethylamino-2-propanol (950 mg, 6.54 mmol), DDC (900 mg, 4.36 mmol) and HOBt. (884 mg, 6.54 mmol) in chloroform (60 mL) was stirred at rt for 12 hrs. The reaction was poured into sat. Sodium bicarbonate (60 mL) and to it was added 1N NaOH (8 mL). It was then extracted with EtOAc (3×100 mL), washed with water and brine, dried and concentrated to give 400 mg of 5-Formyl-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid (3-diethylamino-2-hydroxy-propyl)-amide.

Workup

  1. extractionIt was then extracted with EtOAc (3×100 mL)
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba2e2fb95d7141c796e51afcb4c16dbe
Source dataset
uspto-grants-2007_02
Patent number
US07179910B2

Reaction notes

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