Iodoethane → HCID 58902035, compound

HRID 1992410Notes

Reaction equation

HRID 1992410 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:16][C:17](=[O:25])[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:27][CH3:28]>CCO.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([O:25][CH2:27][CH3:28])[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 136038645HCID 136038645, compound

Product 1

HCID 58902035HCID 58902035, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(3-benzyloxy-phenyl)-8-chloro-2H-imidazo[1,5-a]pyrazin-3-one (50.0 mg, 0.14 mmol) and silver carbonate (85 mg, 0.31 mmol) in anhydrous EtOH (1 mL) was charged with iodoethane (0.012 mL, 0.15 mmol) and stirred at rt for 48 h. The reaction mixture was partitioned between DCM and H2O and separated. The aqueous layer was washed with DCM (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo and the crude material was purified by chromatography on silica gel [eluting with 2% EtOAc in DCM], to yield the desired product as a yellow oil/gum; 1H NMR (CDCl3, 400 MHz) δ 1.51 (t, J=7.2 Hz, 3H), 4.68 (q, J=7.2 Hz, 2H), 5.13 (s, 2H), 7.00-7.05 (m, 1H), 7.13 (d, J=5.2 Hz, 1H), 7.27-7.48 (m, 9H); MS (ES+) m/z=380.07 (100) [MH+], HPLC: tR=4.04 min (MicromassZQ, polar—5 min).

Workup

  1. customThe reaction mixture was partitioned between DCM and H2O
  2. customseparated
  3. washThe aqueous layer was washed with DCM (3×)
  4. washthe combined organic layers were washed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe crude material was purified by chromatography on silica gel [eluting with 2% EtOAc in DCM]

Sources & evidence

ORD record
ord-eb35503074bb4c80acb8dca09ef57b48
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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