Hydrogen Peroxide → HCID 57752649, compound

HRID 226059Notes

Reaction equation

HRID 226059 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:29])=[CH2:28])[C:19]=4[S:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].S(C)C.[OH-:33].[Na+].OO>C1COCC1.O.CO>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH2:28][OH:33])[C:19]=4[S:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 57752702HCID 57752702, compound

Product 1

HCID 57752649HCID 57752649, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(1-ethyl-propyl)-3-(7-isopropenyl-2-methyl-benzo[b]thiophen-3-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.58 g, 1.45 mmol) in THF (20 mL) is cooled to −78° C., and treated with 2.0 M BH3.SMe2 (2.2 mL, 4.3 mmol). The reaction is stirred in the cooling bath, allowed to warm up gradually to RT and stirred at RT overnight. It is cooled to 0° C., treated with CH3OH (10 mL), 5 M NaOH (10 mL), and 30% H2O2 (10 mL). The resulting mixture is stirred at 0° C. for 15 ml, and then at RT for 4 h. It is diluted with H2O (100 mL); extracted with EtOAc (3×100 mL). The combined organic layers is washed with 5% Na2SO3 (100 mL), H2O (100 mL); dried with Na2SO4; filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.35 g, 0.83 mmol, 57%). 1H NMR (CDCl3): δ 0.91 (t, J=7.0 Hz, 3H), 0.92 (t, J=7.0 Hz, 3H), 1.44 (d, J=3.5 Hz, 1.5H), 1.46 (d, J=3.5 Hz, 1.5 Hz), 1.75-1.95 (m, 4H), 2.38 (s, 3H), 2.42 (s, 3H), 2.44 (s, 3H), 3.25-3.40 (m, 1H), 3.40 (bs, 1H), 3.82-4.03 (m, 2H), 6.68 (s, 1H), 7.11 (d, J=7.5 Hz, 1H), 7.19 (d, J=7.5 Hz, 1H), 7.27 (t, J=7.5 Hz, 1H) ppm. ES-MS (m/z): calcd for C25H31N3OS (M+H)+: 422.6. found: 422.3.

Workup

  1. stirringstirred at RT overnight
  2. temperatureIt is cooled to 0° C.
  3. stirringThe resulting mixture is stirred at 0° C. for 15 ml
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers is washed with 5% Na2SO3 (100 mL), H2O (100 mL)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-fb892456e8af44f2ade27fd751989715
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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