Hydrochloric Acid → 6-((2'S,6'R)-3,3''-dimethyl-3', 4', 5', 6'-tetrahydro-2H-2,2';6',2''-terpyridin-1'-ylmethyl)-1,2-benzisoxazol-3-ylamine

HRID 1987343Notes

Reaction equation

HRID 1987343 reaction equation
[CH3:1][C:2]1[C:3]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([O:30][N:31]=C(C)C)[CH:23]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>CCO>[CH3:20][C:19]1[CH:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][C@H:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]2[CH2:21][C:22]2[CH:29]=[CH:28][C:25]3[C:26]([NH2:27])=[N:31][O:30][C:24]=3[CH:23]=2)[NH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865971254-((2'R,6'S)-3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-2-isopropylideneaminooxy-benzonitrile

Product 1

HCID 865971266-((2'S,6'R)-3,3''-dimethyl-3', 4', 5', 6'-tetrahydro-2H-2,2';6',2''-terpyridin-1'-ylmethyl)-1,2-benzisoxazol-3-ylamineYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-((2′R,6′S)-3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-2-isopropylideneaminooxy-benzonitrile (0.145 g, 0.320 mmol) in EtOH (4 mL) was added aqueous HCl (3 N, 4 mL), and the mixture was stirred and heated at reflux overnight. The mixture was then cooled to room temperature, EtOH was removed, and saturated aqueous NaHCO3 (20 mL) was added. The aqueous mixture was extracted with CH2Cl2 (4×40 mL), and the combined extract was dried over Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified on silica gel column (100:5:2 CH2Cl2/CH3OH/NH4OH), affording 6-((2′S,6′R)-3,3″-dimethyl-3′, 4′, 5′, 6′-tetrahydro-2H-2,2′;6′,2″-terpyridin-1′-ylmethyl)-1,2-benzisoxazol-3-ylamine as a white solid (0.082 g, 62%).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customEtOH was removed
  4. additionsaturated aqueous NaHCO3 (20 mL) was added
  5. extractionThe aqueous mixture was extracted with CH2Cl2 (4×40 mL)
  6. extractionthe combined extract
  7. dry with materialwas dried over Na2SO4
  8. filtrationAfter filtration the solvent
  9. customwas removed by evaporation under vacuum
  10. customthe residue was purified on silica gel column (100:5:2 CH2Cl2/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-476898d521b3447f9ad9cb9d9a51f360
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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