m-Chloroperbenzoic acid → HCID 25024718, compound

HRID 871896Notes

Reaction equation

HRID 871896 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[S:16][CH:17]=[C:18]([CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([S:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)[N:19]=3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].ClC1C=C(C(OO)=[O:41])C=CC=1>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[S:16][CH:17]=[C:18]([CH2:20][O:21][C:22]4[CH:23]=[CH:24][C:25]([S:28]([C:29]([F:31])([F:32])[F:30])=[O:41])=[CH:26][CH:27]=4)[N:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 25024519HCID 25024519, compound

Product 1

HCID 25024718HCID 25024718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-Ethyl-2-{4-[4-(4-trifluoromethylsulfanyl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine (Example 16) in DCM at room temperature was added 3-chloro-benzenecarboperoxoic acid (2 eq.). The reaction was allowed to stir for 1.5 hours and an additional portion of 3-chloro-benzenecarboperoxoic acid (1 eq.) was added to the reaction mixture. The reaction was stirred at room temperature for an additional 4 hours. The organic solution was washed with sodium bicarbonate; the organic layer was isolated, dried over sodium sulfate and filtered. The filtrate was concentrated and the crude product was purified by column chromatography to afford the desired product. 1H NMR (DMSO-d6): δ 8.40 (2H, s), 7.58 (2H, d), 7.22 (1H, s), 7.02 (2H, d), 5.17 (2H, s), 3.74 (2H, m), 3.16 (1H, m), 2.96 (2H, m), 2.57 (2H, m), 2.22 (4H, m), 1.24 (3H, m).

Workup

  1. stirringThe reaction was stirred at room temperature for an additional 4 hours
  2. washThe organic solution was washed with sodium bicarbonate
  3. customthe organic layer was isolated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7b4de1e9bfc540f4a8e85fba95d7f0ae
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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