m-Chloroperbenzoic acid → HCID 24944540, compound

HRID 1097414Notes

Reaction equation

HRID 1097414 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[N:21]4[N:22]=[C:23]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)[N:24]=[C:20]4[N:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:36].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16]3[N:21]4[N:22]=[C:23]([C:25]5[CH:26]=[N+:27]([O-:36])[CH:28]=[CH:29][CH:30]=5)[N:24]=[C:20]4[N:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 25032807HCID 25032807, compound2×

Product 1

HCID 24944540HCID 24944540, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In CH2Cl2, dissolved was 7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 101) (3.3 g, 8.06 mmol), and m-chloroperoxybenzoic acid (3.0 g, 12.09 mmol) was slowly added thereto. The mixture was stirred at room temperature. To the reaction mixture, NaHCO3 (aq) was added, and the resultant mixture was extracted three times with CH2Cl2. The extract was washed twice with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to remove solvent. The mixture was purified via silica gel column chromatography (CH2Cl2/MeOH, 50/1) to obtain 3-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyri midine-2-yl]-pyridine-N-oxide (Compound 102) (2.7 g, 79%).

Workup

  1. additionwas slowly added
  2. extractionthe resultant mixture was extracted three times with CH2Cl2
  3. washThe extract was washed twice with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe mixture was purified via silica gel column chromatography (CH2Cl2/MeOH, 50/1)

Sources & evidence

ORD record
ord-81b401fb431d4385bcf5423543a7add2
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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