Water → HCID 66608173, compound

HRID 905729Notes

Reaction equation

HRID 905729 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=N[CH2:22][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)C=O.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][CH2:22][CH2:26]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 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 66608173HCID 66608173, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (1.27 g, 6 mmol) in N,N-dimethylformamide (3 ml) and dichloromethane (30 ml) was added with 2-pyrrolidine-1-yl-ethamine (0.83 ml, 6.6 mmol), N-ethyl-N′-(dimethylaminopropyl)-carbodiimide hydrochloride (3 g, 12 mmol) and 1-hydroxybenzotriazol (0.9 g, 6 mmol) in the ice/water-bath. Upon completion of the addition, the reaction mixture was stirred at room temperature overnight, then added with cold water (20 ml), extracted with dichloromethane (50 ml×3). The combined organic extracts were washed with saturated sodium bicarbonate solution (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-pyrrolidin-1-yl-ethylcarbamoyl)-methyl]-1H-pyrrole-3-carboxylic acid ethyl ester (1.898 g, 100%) 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 solution (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-3d39a80fbc16452ca35c649824e84074
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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