HCID 56840225, compound → HCID 58495701, compound

HRID 2359346Notes

Reaction equation

HRID 2359346 reaction equation
O[C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH2:20])=[O:19])[CH:16]=3)[CH:11]=[N:10][CH:9]=2)[CH2:4][CH2:3]1>FC(F)(F)C(O)=O.ClCCl>[C:21]1([C:2]2[CH2:7][CH2:6][N:5]([C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH2:20])=[O:19])[CH:16]=4)[CH:11]=[N:10][CH:9]=3)[CH2:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 56840225HCID 56840225, compound

Product 1

HCID 58495701HCID 58495701, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-Hydroxy-4-phenylpiperidin-1-yl)isoquinoline-6-carboxamide (134 mg, 0.386 mmol) produced in Example 23 was dissolved in trifluoroacetic acid (1 mL)/dichloromethane (1.5 mL), and the resulting mixture was heated to reflux overnight. Upon completion of the reaction, the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V) to give the desired title compound (108 mg, yield 85%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customUpon completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V)

Sources & evidence

ORD record
ord-435623b6fd4645fabb7c3029e5a0ee30
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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