Hydroxylamine → HCID 178510375, compound

HRID 1913170Notes

Reaction equation

HRID 1913170 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]3[NH:24][CH:25]=[C:26]([C:28](F)(F)F)[N:27]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1.[NH2:32]O>CC#N>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([C:14]([N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][C:23]3[NH:24][CH:25]=[C:26]([C:28]#[N:32])[N:27]=3)[CH2:20][CH2:21]2)=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 178519409HCID 178519409, compound

Product 1

HCID 178510375HCID 178510375, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

This compound is synthesized as described by adaptation of the following reference: Matthews et al, J. Org. Chem., 1986, 51, 3228. To a stirred solution of (2′-fluorobiphenyl-4-yl)(4-{[4-(trifluoromethyl)-1H-imidazol-2-yl]methyl}piperidin-1-yl)methanone (0.114 g, 0.27 mmol) in MeCN (10 mL) is added hydroxylamine (5% aqueous solution, 40 mL). The reaction is heated at 60° C. for 4 h then allowed to cool to room temperature. The mixture is extracted with DCM and washed with saturated aqueous NaHCO3. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product. Purification by column chromatography (silica, eluent: DCM, 0-4% MeOH) gives 12.8 mg (12%) of 2-({1-[(2′-fluorobiphenyl-4-yl)carbonyl]piperidin-4-yl}methyl)-1H-imidazole-4-carbonitrile.

Workup

  1. customThis compound is synthesized
  2. temperatureto cool to room temperature
  3. extractionThe mixture is extracted with DCM
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customPurification by column chromatography (silica, eluent: DCM, 0-4% MeOH)

Sources & evidence

ORD record
ord-e141816d41d84e688a246484a268e7fe
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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