Dipropylamine → HCID 86659884, compound

HRID 2360163Notes

Reaction equation

HRID 2360163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([OH:15])=O.[CH2:16]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:17][CH3:18].CCN=C=NCCCN(C)C>CN(C)C=O.C(OCC)C>[CH2:16]([N:19]([CH2:20][CH2:21][CH3:22])[C:13]([CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1)=[O:15])[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 189865-Methoxyindoleacetic acid

Product 1

HCID 86659884HCID 86659884, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxyindole-3-acetic acid (500 mg, 2.44 mmol) in 4.8 mL of N,N-dimethylformamide was added di-n-propylamine (0.60 mL, 7.2 mmol) and EDCI (1.90 g, 9.6 mmol) at room temperature. After the reaction mixture was stirred at the same temperature for 12 h, the reaction mixture was diluted with diethyl ether, and washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (360 mg, 51%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d9d2ff3d71e243f1bef09c6c7208c4a3
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…