m-Chloroperbenzoic acid → HCID 73293984, compound

HRID 1398054Notes

Reaction equation

HRID 1398054 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]([CH:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)=[N:10]1.ClC1C=C(C=CC=1)C(OO)=[O:35]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:15]=[N+:16]([O-:35])[CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]([CH:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)=[N:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 73292409HCID 73292409, compound

Product 1

HCID 73293984HCID 73293984, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(2-methoxyphenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-pyridine (9 mg, 0.023 mmol) (Example 44) in 1 mL of DCM at Rt was added m-chloroperoxybenzoic acid (60%)(7.9 mg, 0.028 mmol) and the mixture stirred for 1 hr at Rt. The solvents were evaporated and the crude product purified by RP-HPLC, eluting with a linear gradient of 30-70% CH3CN in 0.1% TFA/H2O over 10 mins to give 8 mg (71%) of the title compound as white solid containing 0.5 eq of TFA.

Workup

  1. customThe solvents were evaporated
  2. customthe crude product purified by RP-HPLC
  3. washeluting with a linear gradient of 30-70% CH3CN in 0.1% TFA/H2O over 10 mins

Sources & evidence

ORD record
ord-702ca5da92dd43d19ad8fb95faf5c8d6
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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