Ethyl iodoacetate → HCID 58788370, compound

HRID 2374741Notes

Reaction equation

HRID 2374741 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][C:13]([NH:15][C:16]1[C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]([CH3:24])[N:17]=1)=[O:14].I[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C=O)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:15]([C:16]1[C:20]([C:21](=[O:22])[NH2:23])=[CH:19][N:18]([CH3:24])[N:17]=1)[C:13](=[O:14])[CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:4]=1[F:3])[CH3:31]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 58788307HCID 58788307, compound

Product 1

HCID 58788370HCID 58788370, compoundYield 279.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 260 mg, 6.5 mmol) in anhydrous DMF (5 ml) under argon at 0° C. was added a solution of 3-[3-(2,3-difluorophenyl)-propanoylamino]-1-methyl-1H-pyrazole-4-carboxylic acid amide (Int. B58) (2.0 g, 6.49 mmol) in anhydrous DMF (5 ml). The reaction mixture was allowed to warm to room temperature over 30 min and then ethyl iodoacetate (0.15 ml, 1.27 mmol) was added at 0° C. The mixture was stirred at ambient temperature overnight, washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (fine silica, dichloromethane-methanol) to give the title compound as a cream solid (1.4 g, 55%). 1H-NMR (DMSO) δ 1.18 (3H, t), 2.41 (2H, t), 2.87 (2H, t), 3.82 (3H, s), 4.10 (2H, q), 4.26 (2H, s), 6.99-7.24 (4H, m), 7.55 (1H, s), 8.16 (1H, s); MS (APCI+) found (M+1)=395; C18H20F2N4O4 requires 394.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography (fine silica, dichloromethane-methanol)

Sources & evidence

ORD record
ord-eb0d3bb7d10b478c823c5bffbb7f74e2
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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