Iodoethane → HCID 58203459, compound

HRID 2194793Notes

Reaction equation

HRID 2194793 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:11]([C:13]1[NH:14][C:15](=[O:23])[NH:16][C:17](=[O:22])[C:18]=1[CH:19]([CH3:21])[CH3:20])=[O:12].C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH3:32]>CN(C=O)C>[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:11]([C:13]1[N:14]([CH2:31][CH3:32])[C:15](=[O:23])[NH:16][C:17](=[O:22])[C:18]=1[CH:19]([CH3:20])[CH3:21])=[O:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 58203554HCID 58203554, compound

Product 1

HCID 58203459HCID 58203459, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Compound 98 (0.067 g, 0.202 mmol) and potassium carbonate (0.0279 g, 0.202 mmol) in DMF (1.0 mL) was added iodoethane (14 μL, 0.168 mmol) and reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, dried (MgSO4) and concentrated. The resulting residue was purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O) to give a white powder after lyophilization (20.5 mg, 28%). 1H NMR (300 MHz, CD3CN): 9.15 (s, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 3.52 (br s, 2H), 2.47 (s, 3H), 2.3-2.2 (m, 1H), 1.1-1.0 (s, 9H); Mass Spectrum: 360.2, 362.2 (M+H).

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O)
  7. customto give a white powder after lyophilization (20.5 mg, 28%)

Sources & evidence

ORD record
ord-036a7bb83a6545f68bb76dde4d12f8ca
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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