Isoamyl Nitrite → HCID 25234836, compound

HRID 1930272Notes

Reaction equation

HRID 1930272 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([N:23]4[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]4=[O:30])[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=3[O:17][CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.N(OCCC(C)C)=O>O1CCOCC1>[S:3]1[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([N:23]4[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]4=[O:30])[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=3[O:17][CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=[CH:2]1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 25234760HCID 25234760, compound

Product 1

HCID 25234836HCID 25234836, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from Example 53 (30 mg, 0.071 mmol) in anhydrous 1,4-dioxane (3 mL) under N2 was added isoamyl nitrite (19 μL, 0.142 mmol). The resulting mixture was stirred at reflux for 1 h, and concentrated in vacuo. The crude product was purified by C-18 reverse-phase HPLC using an acetonitrile:H2O (0.1% TFA) gradient to give the title compound (14 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ 11.42 (d, J=1.84 Hz, 1H) 9.44 (s, 1H) 8.34 (d, J=1.47 Hz, 1H) 8.19 (d, J=8.46 Hz, 1 H) 7.79 (d, J=7.72 Hz, 1H) 7.73 (dd, J=8.46, 1.84 Hz, 1H) 7.32-7.37 (m, 2H) 5.65 (dd, J=7.91, 2.39 Hz, 1H) 3.24 (s, 3H) 1.42 (s, 9H).

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by C-18 reverse-phase

Sources & evidence

ORD record
ord-b110ad1895ee4cb8a859c4263a8f31fe
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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