Monoperoxyphthalic Acid Magnesium Salt → HCID 86615168, compound

HRID 1868131Notes

Reaction equation

HRID 1868131 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH2:17][C@H:16]2[CH3:31])(=[O:14])=[O:13])=[CH:8][CH:7]=1)([OH:5])[CH3:4].C1C=C(C([O-])=[O:41])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO>[F:33][C:2]([F:1])([F:32])[C:3]([C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N+:24]([O-:41])=[CH:23][C:22]=3[C:27]([F:28])([F:29])[F:30])[CH2:17][C@H:16]2[CH3:31])(=[O:13])=[O:14])=[CH:10][CH:11]=1)([OH:5])[CH3:4]

Participants

4

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 86615169HCID 86615169, compound

Product 1

HCID 86615168HCID 86615168, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a flask containing 1,1,1-trifluoro-2-[4-({(2R)-2-methyl-4-[3-(trifluoromethyl)pyridin-4-yl]piperazin-1-yl}sulfonyl)phenyl]propan-2-ol (60 mg, 0.12 mmol) and 1.5 mL of DCM/MeOH (9/1, v/v) was added MMPP (74.6 mg, 0.15 mmol). The resulting slurry was stirred at room temperature over night. Reaction was complete as determined by TLC. This was filtered, washed with DCM. The filtrate was concentrated under reduced pressure. Purification by flash column chromatography to yield 1,1,1-trifluoro-2-[4-({(2R)-2-methyl-4-[1-oxido-3-(trifluoromethyl)pyridin-4-yl]piperazin-1-yl}sulfonyl)phenyl]propan-2-ol as a white solid (13.5 mg, 21.9 yield). HRMS: calcd for C20H21F6N3O4S+H+, 514.12297. found (ESI-FTMS, [M+H]1+), 514.12174.

Workup

  1. customReaction
  2. filtrationThis was filtered
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customPurification by flash column chromatography
  6. customto yield

Sources & evidence

ORD record
ord-dccb4d9b2066485b95fad010f172200b
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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