Trifluoroacetic acid → HCID 11178519, compound

HRID 412597Notes

Reaction equation

HRID 412597 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][S:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][N:27]([C:31](=[O:33])[CH3:32])[CH2:28]3)=[CH:23][CH:22]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.F[C:35](F)(F)[C:36](O)=O>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([C:11]1([CH2:19][S:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][N:27]([C:31](=[O:33])[CH3:32])[CH2:28]3)=[CH:23][CH:22]=2)[CH2:10][CH2:9][N:8]([C:36]2[CH:35]=[CH:13][N:8]=[CH:9][CH:10]=2)[CH2:13][CH2:12]1)=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11374968HCID 11374968, compound

Product 1

HCID 11178519HCID 11178519, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(2-acetyl-1,2,3,4-tetrahydroisoquinolin-7-ylthiomethyl)-4-ethoxycarbonylpiperidine-1-carboxylic acid tert-butyl ester (221 mg) in chloroform (0.5 ml) was added trifluoroacetic acid (1 ml), and the mixture was stirred at room temperature for 10 min. After completion of the reaction, the solvent was evaporated and to the obtained residue were added ethanol (3 ml), triethylamine (0.39 ml) and 4-chloropyridine hydrochloride (70 mg). The mixture was stirred in a sealed tube at 150° C. for 2 days. After completion of the reaction, the solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (5% methanol-chloroform) and dried under reduced pressure to give the title compound (63 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated and to the obtained residue
  3. additionwere added ethanol (3 ml), triethylamine (0.39 ml) and 4-chloropyridine hydrochloride (70 mg)
  4. stirringThe mixture was stirred in a sealed tube at 150° C. for 2 days
  5. customAfter completion of the reaction
  6. customthe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (5% methanol-chloroform)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-edfcf625d7724997b2138b64239c0b21
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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