HCID 68194434, compound → HCID 105456868, compound

HRID 2370652Notes

Reaction equation

HRID 2370652 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=2)[CH2:5]1)[CH3:2]>CO.[Pd]>[CH2:16]([N:3]([CH2:1][CH3:2])[CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH2:13])[CH:10]=2)[CH2:5]1)[CH3:17]

Participants

4

Reactant 1

HCID 68194434HCID 68194434, compound

Product 1

HCID 105456868HCID 105456868, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 226B (2.0 g, 8.54 mmol) in methanol (50 ml) was added Pd/C (10%, 2 g). The mixture was bubbled with hydrogen and stirred overnight. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated. The crude product was purified by HPLC (C18 column, mobile phase A: 10 mM NH4HCO3 in water, mobile phase B: acetonitrile, 50-75% B) to provide the title compound. MS m/z: 205 (M+H)+. 1H NMR (400 MHz, CDCl3): δ 6.95 (d, J=8.0 Hz, 1H), 6.54 (s, 1H), 6.46 (dd, J=7.6, 2.0 Hz, 1H), 3.61-3.54 (m, 1H), 2.97-2.91 (m, 2H), 2.83-2.73 (m, 2H), 2.64 (q, J=7.2 Hz, 4H), 1.05 (t, J=6.8 Hz, 6H).

Workup

  1. customThe mixture was bubbled with hydrogen
  2. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  3. concentrationconcentrated
  4. customThe crude product was purified by HPLC (C18 column, mobile phase A: 10 mM NH4HCO3 in water, mobile phase B: acetonitrile, 50-75% B)

Sources & evidence

ORD record
ord-5639658262d84bf08784e1f483ea5ffb
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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