Triethylamine → HCID 178513255, compound

HRID 730074Notes

Reaction equation

HRID 730074 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:27]#[N:28])[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].Cl.[NH2:32][OH:33].C(N(CC)CC)C>C(O)C>[OH:33][NH:32][C:27]([C:22]1[C:21]2[O:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:8]3[CH2:9][CH:10]4[N:5]([C:3](=[O:4])[C:2]([F:30])([F:29])[F:1])[CH:6]([CH2:12][CH2:11]4)[CH2:7]3)[C:26]=2[CH:25]=[CH:24][CH:23]=1)=[NH:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57833595HCID 57833595, compound

Product 1

HCID 178513255HCID 178513255, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-4-carbonitrile in ethanol (0.1 to 2 M solution) may be treated with hydroxylamine hydrochloride (1 to 2 equiv) and triethylamine (2 to 3 equiv) and may be heated to reflux for a period of 1 to 10 hr. After cooling, the mixture may be evaporated under reduced pressure, and the residue may be partitioned between equal amounts of water and an organic solvent such as ethyl acetate. The organic layer may be separated, dried over an appropriate drying agent such as magnesium sulfate, filtered, and evaporated. The residue may be purified via column chromatography to yield Compound 1f.

Workup

  1. temperaturemay be heated
  2. temperatureto reflux for a period of 1 to 10 hr
  3. temperatureAfter cooling
  4. customthe mixture may be evaporated under reduced pressure
  5. customthe residue may be partitioned between equal amounts of water
  6. customThe organic layer may be separated
  7. dry with materialdried over an appropriate drying agent such as magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue may be purified via column chromatography

Sources & evidence

ORD record
ord-a5c9651005d041ebaa5f5d0ad9e3e60f
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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