Water → 4-methyl-2-[(2-morpholin-4-yl-ethylcarbamoyl)-methyl]-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2365003Notes

Reaction equation

HRID 2365003 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][C:13]([OH:15])=O)=[O:5])[CH3:2].Cl.C(N=C=NC[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])C.O[N:29]1[C:33]2C=CC=CC=2N=N1.O.CN(C)[CH:41]=[O:42]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][C:13](=[O:15])[NH:29][CH2:33][CH2:27][N:25]1[CH2:24][CH2:23][O:42][CH2:41][CH2:26]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498403282-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 666068544-methyl-2-[(2-morpholin-4-yl-ethylcarbamoyl)-methyl]-1H-pyrrole-3-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (2.67 g, 12.67 mmol) in N,N-dimethylformamide (7 ml) and dichloromethane (65 ml) was added with 2-morpholin-4-yl-ethamine (1.81 g, 13.9 mmol), N-ethyl-N′-(dimethylaminopropyl)-carbodiimide hydrochloride (4.84 g, 25.34 mmol) and 1-hydroxybenzotriazol (1.71 g, 12.67 mmol) in an ice/water-bath. Upon completion of the addition, the reaction mixture was stirred at room temperature overnight, added with cold water (50 ml) and extracted with dichloromethane (50 ml×3). The combined organic extracts were washed with saturated sodium bicarbonate (50 ml), water (50 ml), brine (50 ml), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 4-methyl-2-[(2-morpholin-4-yl-ethylcarbamoyl)-methyl]-1H-pyrrole-3-carboxylic acid ethyl ester (3.48 g, 85%) as a brown oil which was used as such.

Workup

  1. additionUpon completion of the addition
  2. extractionextracted with dichloromethane (50 ml×3)
  3. washThe combined organic extracts were washed with saturated sodium bicarbonate (50 ml), water (50 ml), brine (50 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08c74aedd7744a6cb94093b48fdc6541
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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