m-Chloroperbenzoic acid → HCID 178509919, compound

HRID 505526Notes

Reaction equation

HRID 505526 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3[CH2:21][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][N:23]=2)[CH:9]=1)[C:5]#[N:6].C1C=C(Cl)C=C(C(OO)=[O:39])C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3[CH2:21][C:22]2[C:30]3[C:25](=[N+:26]([O-:39])[CH:27]=[CH:28][CH:29]=3)[NH:24][N:23]=2)[CH:9]=1)[C:5]#[N:6]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178509920HCID 178509920, compound

Product 1

HCID 178509919HCID 178509919, compound

Procedure

To a suspension of 3-chloro-5-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-indazol-4-yl]oxy}benzonitrile (96 mg, 0.221 mmol) was added mCPBA (59.8 mg, 0.243 mmol) and stirred at room temperature for 18 hours. The suspension was concentrated in vacuo and then resuspended in DMF (5 mL). This suspension was filtered and then purified by reverse phase HPLC (Luna column, 10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA). The desired fractions were concentrated to dryness and the resulting solid was suspended in MeOH (1 mL) and filtered to give the title compound.

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. filtrationThis suspension was filtered
  3. custompurified by reverse phase HPLC (Luna column, 10μ, C18, 250×21.2 cm)
  4. washeluting with 5-95% ACN/water with 0.1% TFA)
  5. concentrationThe desired fractions were concentrated to dryness
  6. filtrationfiltered

Sources & evidence

ORD record
ord-299a0f34b49748d6b4a1d4742a9354fd
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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