1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10627406, compound

HRID 613621Notes

Reaction equation

HRID 613621 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([NH:14][CH2:15][C:16]2[N:17]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][O:29][C:30]4[CH:31]=[CH:32][CH:33]=[C:34]5[C:39]=4[N:38]=[C:37]([CH3:40])[CH:36]=[CH:35]5)[C:22]=3[Cl:41])[CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:6][CH:5]=1)(O)=[O:2].Cl.CN.[CH2:45]([N:47]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Cl:41][C:22]1[C:23]([CH2:28][O:29][C:30]2[CH:31]=[CH:32][CH:33]=[C:34]3[C:39]=2[N:38]=[C:37]([CH3:40])[CH:36]=[CH:35]3)=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[N:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[CH2:15][NH:14][C:12](=[O:13])/[CH:11]=[CH:10]/[C:7]1[CH:8]=[N:9][C:4]([C:1](=[O:2])[NH:47][CH3:45])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 10579237HCID 10579237, compound

Product 1

HCID 10627406HCID 10627406, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(E)-3-(6-carboxypyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (60 mg) and methylamine hydrochloride (7.59 mg) in N,N-dimethylformamide (2 ml) were added 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (19 mg) and 1-hydroxybenzotriazole (20.7 mg) at ambient temperature, and the mixture was allowed to stand for 1 day at the same temperature. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V) to give 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[(E)-3-[6-(methylcarbamoyl)pyridin-3-yl]acryloylaminomethyl]pyrrole (58 mg) as amorphous powder.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

Sources & evidence

ORD record
ord-4381b1beeaa048cf9e92f0552aafa34e
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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