HCID 68617097, compound → HCID 68616187, compound

HRID 1476734Notes

Reaction equation

HRID 1476734 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[CH:22]=[CH:21][C:9]2[N:10]([CH2:17][CH2:18][CH2:19][OH:20])[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[N:12][C:8]=2[CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:22]=[CH:21][C:9]2[N:10]([CH2:17][CH2:18][CH2:19][OH:20])[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[N:12][C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 68617097HCID 68617097, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68616187HCID 68616187, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-acrylic acid methyl ester (prepared according to the Example 1, step 1-3) (126.6 mg, 0.4 mmol) and 10% Pd/C (40 mg) in 10 mL of MeOH was hydrogenated using a hydrogen balloon overnight. After filtration through short-column silica gel, the filtrate was evaporated under reduced pressure to give 3-[1-(3-hydroxy-propyl)-2-isobutyl-1H-benzimidazol-5-yl]-propionic acid methyl ester (127 mg) in quantitative yield: MS m/z (M+H)+: 319; 1H NMR (400 MHz, MeOD) δ 0.95 (6H, d, J=6.4 Hz), 1.92 (2H, m), 2.19 (1H, m), 2.60 (2H, t, J=8.0 Hz), 2.74 (2H, d, J=7.2 Hz), 2.96 (2H, t, J=7.6 Hz), 3.50 (2H, t, J=4.1 Hz), 3.54 (3H, s), 4.25 (2H, t, J=7.2 Hz), 7.05 (1H, d, J=8.0 Hz), 7.30-7.40 (2H, m); 13C NMR (100 MHz, MeOD) δ 20.9 (2C), 27.3, 30.1, 31.5, 34.6, 35.3, 39.5, 50.1, 57.4, 109.1, 116.4, 122.1, 132.6, 134.2, 141.3, 154.2, 173.2.

Workup

  1. filtrationAfter filtration through short-column silica gel
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9585482ffe2b42d890568bfff5950dea
Source dataset
uspto-grants-2016_08
Patent number
US09402829B2

Reaction notes

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