Water → HCID 53932730, compound

HRID 843157Notes

Reaction equation

HRID 843157 reaction equation
[OH:1][CH:2]([CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[CH2:3][O:4][C:5]1[C:10]2[C:11]([CH3:17])=[C:12]([C:14]([OH:16])=O)[O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl.[CH2:24]([NH2:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(N(CC)CC)C>[CH2:24]([NH:26][C:14]([C:12]1[O:13][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[C:10]=2[C:11]=1[CH3:17])=[O:16])[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 22615054HCID 22615054, compound

Product 1

HCID 53932730HCID 53932730, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid (5 mg), ethylamine hydrochloride (42 mg), water-soluble carbodiimide hydrochloride (10 mg), 1-hydroxybenzotriazole (8 mg) and triethylamine (100 μl) in DMF (1 ml) was stirred at room temperature for five hours. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH:H2O=65:30:5 as a developing solvent) to give 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethylamide (2 mg) as a white powder. MALDI-TOF-MS: m/z 335 (MH+); 1H-NMR (CDCl3): δ 1.27 (3H, t, J=7 Hz), 1.34 (6H, d, J=6 Hz), 2.72 (3H, s), 3.13 (1H, dd, J1=12 Hz, J2=9 Hz), 3.32 (2H, m), 3.49 (2H, dq, J1=7 Hz, J2=6 Hz), 4.05 (1H, dd, J1=10 Hz, J2=6 Hz), 4.15 (1H, dd, J1=10 Hz, J2=5 Hz), 4.53 (1H, br s), 6.55 (1H, d, J=8 Hz), 6.56 (1H, m), 7.00 (1H, d, J=8 Hz), 7.22 (1H, t, J=8 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-90882fad6a81449ab01f1ac2826b1d88
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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