Acetonitrile → HCID 135890119, compound

HRID 539885Notes

Reaction equation

HRID 539885 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([CH2:15][CH3:16])=[C:10]([CH2:17][CH3:18])[N:9]=2)[CH:7]=1.C([O-])=O.[NH4+].[C:27](#N)[CH3:28]>[Pd]>[CH2:15]([C:11]1[C:12](=[O:14])[NH:13][C:8]([C:6]2[CH:7]=[C:2]([NH:1][CH2:27][CH3:28])[CH:3]=[CH:4][C:5]=2[O:19][CH2:20][CH2:21][CH3:22])=[N:9][C:10]=1[CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2723923Ammonium formateHCID 136197415HCID 136197415, compound

Product 1

HCID 135890119HCID 135890119, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound (2.2 g, 7.3 mmol) of example 42 was dissolved in 50 ml of 80% acetonitrile aqueous solution, and added with 0.14 g of 5% Pd/C and 5 g of ammonium formate, followed by stirring at room temperature for 20 h under nitrogen atmosphere. The reaction mixture was filtered off Pd/C and distilled off the solvent. The residue was dissolved in CH2Cl2 (50 ml), washed with water (50 ml) and saturated saline (50 ml), dried with anhydrous Na2SO4, and concentrated to dryness to give a white solid crude, which was passed through a silica gel column (eluant: 10% petroleumether-ethyl acetate) to afford the title compound (1.9 g, yield: 79%). 1H NMR (CDCl3) δ: 8.38 (1H, d), 7.33 (1H, dd), 7.04 (1H, d), 4.19 (2H, t), 4.04 (2H, q), 2.66 (2H, q), 2.59 (2H, q), 2.01 (2H, m), 1.28 (3H, t), 1.19 (3H, t), 1.15 (3H, t), 1.06 (3H, t).

Workup

  1. filtrationThe reaction mixture was filtered off Pd/C
  2. distillationdistilled off the solvent
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  4. washwashed with water (50 ml) and saturated saline (50 ml)
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated to dryness
  7. customto give a white solid crude, which

Sources & evidence

ORD record
ord-56d0f5e934b7460f98b507b71491f5bb
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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