Acetic Acid → HCID 53749246, compound

HRID 843160Notes

Reaction equation

HRID 843160 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][N:24](CC4C=CC=CC=4)[CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 53662796HCID 53662796, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53749246HCID 53749246, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3-(1-benzyl-piperidin-4-ylamino)-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (the compound in Example 100, 100 mg) and acetic acid (2 ml) in ethyl acetate (6 ml) was added 10% Pd on charcoal catalyst (20 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 the pad of celite was rinsed with methanol and dichloromethane. The filtrate combined was concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane-MeOH) to give 3-methyl-4-[3-(piperidin-4-ylamino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (48 mg) as a colorless oil. FAB-MS: m/z 361 (MH+); 1H-NMR (CDCl3): δ 1.36 (2H, m), 1.43 (3H, t, J=7 Hz), 1.97 (2H, m), 2.07 (2H, quintet, J=6.5 Hz), 2.68 (3H, m), 2.74 (3H, s), 2.89 (2H, t, J=7 Hz), 3.17 (2H, br d, J=12.5 Hz), 4.16 (2H, t, J=6 Hz), 4.44 (2H, q, J=7 Hz), 6.62 (1H, d, J=8 Hz), 7.11 (1H, d, J=8 Hz), 7.30 (1H, t, J=8 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washthe pad of celite was rinsed with methanol and dichloromethane
  3. concentrationThe filtrate combined was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (dichloromethane-MeOH)

Sources & evidence

ORD record
ord-ab1271ecd0824639a5a6ddf5fe952718
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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