m-Chloroperbenzoic acid → HCID 67183377, compound

HRID 218793Notes

Reaction equation

HRID 218793 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[C:12]([CH2:14][N:15]([C:29]3[CH:30]=[N:31][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:34]=3)[C:16]([CH:18]3[C:27]4[C:22](=[C:23]([OH:28])[CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:11]=[N:10]2)=[CH:4][CH:3]=1.[Cl:38]C1C=CC=C(C(OO)=[O:46])C=1>C(Cl)(Cl)Cl>[ClH:38].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[C:12]([CH2:14][N:15]([C:29]3[CH:30]=[N+:31]([O-:46])[C:32]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:34]=3)[C:16]([CH:18]3[C:27]4[C:22](=[C:23]([OH:28])[CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 16678569HCID 16678569, compound

Product 1

HCID 67183377HCID 67183377, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-({1-[(4-fluorophenyl)methyl]pyrazol-4-yl}methyl)-5-hydroxy-N-(6-isopropylpyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.55 g) in chloroform (10 mL) was added m-chloroperbenzoic acid (0.29 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was partitioned between water and chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give N-({1-[(4-fluorophenyl)methyl]pyrazol-4-yl}methyl)-5-hydroxy-N-(6-isopropyl-1-oxidopyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride (0.13 g).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fb32d57d597c4b518a6c02011c74c2ac
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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