m-Chloroperbenzoic acid → HCID 57550070, compound

HRID 1676191Notes

Reaction equation

HRID 1676191 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:27]=[CH:26][C:25]([CH2:28][CH2:29][CH3:30])=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[CH:11][C:10]2=[O:31])=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:37]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]4[N:23]=[CH:24][C:25]([CH2:28][CH2:29][CH3:30])=[CH:26][N:27]=4)[CH2:20][CH2:21]3)=[CH:11][C:10]2=[O:31])=[CH:7][CH:8]=1)=[O:37]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57468392HCID 57468392, compound

Product 1

HCID 57550070HCID 57550070, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 1-(4-(methylthio)phenyl)-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (51.4 mg, 0.118 mmol) in CH2Cl2 (15 mL) at 0° C. was added a solution of 3-Chloroperoxybenzoic acid (26.4 mg, 0.118 mmol) in 5 mL CH2Cl2. The reaction was stirred at 0° C. for 15 min and then quenched with Na2SO3 (sat. solution in H2O). The organic layer was washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0 to 10% MeOH in CH2Cl2) to yield 50 mg of desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.16 (s, 2H), 7.77 (d, J=8.31 Hz, 2H), 7.57 (d, J=8.31 Hz, 2H), 7.23 (d, J=7.34 Hz, 1H), 5.94-6.11 (m, 2 H), 4.44-4.64 (m, 1H), 4.07-4.31 (m, 2H), 3.50-3.74 (m, 2H), 2.77 (s, 3H), 2.40 (t, J=7.58 Hz, 2H), 1.98-2.17 (m, 2H), 1.73-1.93 (m, 2H), 1.50-1.64 (m, 2H), 0.93 (t, =7.34 Hz, 3H). MS (ESI) 453 (M+H).

Workup

  1. customquenched with Na2SO3 (sat. solution in H2O)
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo to a white solid
  5. customThe solid was purified by flash chromatography (SiO2, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b0e230f585244b47885946abf2238b70
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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