HCID 21193375, compound → HCID 21193244, compound

HRID 443256Notes

Reaction equation

HRID 443256 reaction equation
[OH:1][CH2:2][C:3]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[N:14]([CH2:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:13]([CH3:24])=[N:12][CH:11]=2)[CH2:5][CH2:4]1.B1([O-])O[O:38]1.O.O.O.O.[Na+]>CO.O>[OH:1][CH2:2][C:3]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:34])([F:35])[F:36])[CH:27]=2)[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[N:14]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH2:21])=[O:38])=[CH:22][CH:23]=3)[C:13]([CH3:24])=[N:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 21193375HCID 21193375, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 21193244HCID 21193244, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-{5-[4-hydroxymethyl-4-(3-trifluoromethoxy-benzyl)-piperidine-1-ylmethyl]-2-methylimidazol-1-ylmethyl}benzonitrile (71 mg, 0.142 mmol; Example 31) and sodium perborate tetrahydrate (92.8 mg, 0.6 mmol) in a mixture of methanol (2.5 mL) and water (1 mL) was heated at 50° C. for 7 h. The resultant mixture was concentrated under vacuum, and the residue was partitioned between chloroform and dilute hydrochloric acid (0.5M). The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 10% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound as white solid.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. customthe residue was partitioned between chloroform and dilute hydrochloric acid (0.5M)
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-c217e975937d42b1930b4ee757f372e5
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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