1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-((S)-2-cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

HRID 1359766Notes

Reaction equation

HRID 1359766 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].[CH:13]1([NH:16][CH2:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)[CH2:15][CH2:14]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:13]1([NH:16][CH2:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:9]([C:5]2[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=2[CH3:8])=[O:11])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic AcidHCID 69869739cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine

Product 1

HCID 865886154-((S)-2-cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (270 mg, 1.61 mmol), cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine (220 mg, 1.57 mmol), HOBt (199 mg, 1.47 mmol), EDAC (344 mg, 1.8 mmol) and TEA (0.5 mL) in DMF (7 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate and extracted with DCM. The combined DCM was dried, concentrated and filtered through silica gel to give 4-((S)-2-cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sodium bicarbonate
  3. extractionextracted with DCM
  4. dry with materialThe combined DCM was dried
  5. concentrationconcentrated
  6. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-4ff22164fff746fc97d49a5b2d59c99e
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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