Ethyl Acetate → HCID 66581135, compound

HRID 1521875Notes

Reaction equation

HRID 1521875 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]3[N:13]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:14]=[C:15]([C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[O:17])[C:11]=3[CH2:10]S[C:8]=12.O[O:31][S:32]([O-:34])=O.[K+].CCOC(C)=O>C1COCC1.O>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]3[N:13]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:14]=[C:15]([C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[O:17])[C:11]=3[CH2:10][S:32](=[O:34])(=[O:31])[C:8]=12

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 66580228HCID 66580228, compound

Product 1

HCID 66581135HCID 66581135, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of N-methyl-3-(morpholin-4-ylcarbonyl)-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazol-6-amine (90 mg, 0.22 mmol) in THF: H2O (1:1, 10 mL) is added oxone (545 mg, 0.88 mmol) and the reaction mixture is stirred at RT for 3 h. After this time, EtOAc is added to the reaction mixture that is washed with water. The organic layer is separated, dried over Na2SO4, concentrated under reduced pressure. The solid residue is purified by silica gel flash chromatography (40% EtOAc in pet.ether) the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.59-7.56 (m, 3H), 7.47-7.44 (m, 2H), 7.26-7.22 (t, J=8.1 Hz,1H), 6.80-6.74 (m, 2H), 5.98-5.96 (d, J=7.6 Hz,1H), 4.87 (s, 2H), 3.95-3.94 (m, 2H), 3.65 (m, 4H), 3.61-3.59 (m, 2H), 2.83-2.82 (d, J=4.7 Hz, 3H). MS (ESI+): 439.0. HPLC (max plot) 95.63%; Rt 4.39 min.

Workup

  1. washis washed with water
  2. customThe organic layer is separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue is purified by silica gel flash chromatography (40% EtOAc in pet.ether) the title compound as a white solid

Sources & evidence

ORD record
ord-894ca34ef31340ed83b0ed28830209f8
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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