HCID 53973988, compound → HCID 22615028, compound

HRID 843142Notes

Reaction equation

HRID 843142 reaction equation
C(OC(=O)[N:10]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:27]2[C:28]([CH3:35])=[C:29]([CH2:31][O:32][CH2:33][CH3:34])[O:30][C:26]=2[CH:25]=[CH:24][CH:23]=1)[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH3:10].[CH2:33]([O:32][CH2:31][C:29]1[O:30][C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([O:21][CH2:20][CH2:19][CH2:18][NH:10][CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:27]=2[C:28]=1[CH3:35])[CH3:34]

Participants

6

Reactant 2

HCID 53973988HCID 53973988, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 222AmmoniaYield 25%HCID 22615028HCID 22615028, compoundYield 130.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-(2-ethoxymethyl-3-methyl-benzofuran-4-yloxy)-propyl]-pyridin-3-ylmethyl-carbamic acid benzyl ester (19 mg) in ethyl acetate (1 ml) was added 5% Pd on charcoal catalyst (10 mg) under N2. The nitrogen atmosphere was replaced by hydrogen (1 atom) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered through a pad of celite and washed with methanol and dichloromethane. The filtrate combined was concentrated in vacuo. The residue was purified by preparative thin layer chromatography (using dichloromethane : MeOH : ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give [3-(2-ethoxymethyl-3-methyl-benzofuran-4-yloxy)-propyl]-pyridin-3-ylmethyl-amine (9 mg) as a colorless oil. ESI-MS: m/z 355 (MH+); 1H-NMR (CDCl3): δ 1.24 (3H, t, J=7 Hz), 2.06 (2H, quintet, J=6.5 Hz), 2.31 (3H, s), 2.89 (2H, t, J=7 Hz), 3.56 (2H, q, J=7 Hz), 3.85 (2H, s), 4.14 (2H, t, J=6 Hz), 4.54 (2H, s), 6.58 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.14 (1H, t, J=8 Hz), 7.21 (1H, dd, J1=8 Hz, J2=5 Hz), 7.68 (1H, dd, J1=8 Hz, J2=2 Hz), 8.49 (1H, dd, J1=5 Hz, J2=2 Hz), 8.57 (1H, d, J=2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with methanol and dichloromethane
  3. concentrationThe filtrate combined was concentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-e29f70ab42904c1fad1b132c79287528
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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