Trifluoroacetic acid → HCID 178444659, compound

HRID 1826352Notes

Reaction equation

HRID 1826352 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:20])[CH:13]3[CH:9]2[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]3)[CH:5]=[CH:4][C:3]=1[NH2:21].[F:22][C:23]([F:28])([F:27])[C:24](O)=O>>[CH2:14]([N:11]1[CH2:10][CH:9]2[CH:13]([C:8]2([C:6]2[CH:5]=[CH:4][C:3]3[NH:21][C:24]([C:23]([F:28])([F:27])[F:22])=[N:1][C:2]=3[CH:7]=2)[CH3:20])[CH2:12]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22141195HCID 22141195, compound

Product 1

HCID 178444659HCID 178444659, compoundYield 54%

Procedure

A solution of 2-amino-4-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 48, 99.0 mg, 0.345 mmol) in trifluoroacetic acid (2.0 ml) was heated under reflux for 1 hour. The mixture was cooled and the solvent was removed in vacuo. The residue was suspended in 2N sodium hydroxide (5 ml) and the aqueous layer was extracted with diethyl ether (3×5 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate to afford the title compound (67 mg, 54%) as a colourless oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed in vacuo
  4. extractionthe aqueous layer was extracted with diethyl ether (3×5 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica column chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-7fe3e31222b94999a579e8b47ccc6012
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

Loading…