Triethylamine → HCID 46847186, compound

HRID 2359343Notes

Reaction equation

HRID 2359343 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23](OCC[Si](C)(C)C)=[O:24])[CH:21]=4)[CH:16]=[N:15][CH:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].C([N:36](CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1.CN(C)C=O>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]([NH2:36])=[O:24])[CH:21]=4)[CH:16]=[N:15][CH:14]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58495808HCID 58495808, compound

Product 1

HCID 46847186HCID 46847186, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(Trimethylsilyl)ethyl 4-(4-phenylpiperazin-1-yl)isoquinoline-6-carboxylate (2.37 g, 5.47 mmol) produced in Example 3 (3d) was dissolved in tetrahydrofuran (27 mL), to which a 1.0M n-tetrabutylammonium fluoride/tetrahydrofuran solution (16.4 mL, 16.4 mmol) was then added, followed by stirring at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in N,N-dimethylformamide (47 mL) under a nitrogen atmosphere, to which ammonium chloride (2.92 g, 54.7 mol), triethylamine (9.14 mL, 65.6 mmol), 1-hydroxybenzotriazole (251 mg, 1.64 mmol), and N-[3-dimethylaminopropyl]-N′-ethylcarbodiimide hydrochloride (5.24 g, 27.3 mmol) were added, followed by stirring at room temperature for 13 hours. The resulting reaction liquid was filtered and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V) and recrystallized from a mixed solvent of ethanol-dichloromethane to give the desired title compound (1.13 g, yield 62%).

Workup

  1. additionwas then added
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. additionwere added
  5. stirringby stirring at room temperature for 13 hours
  6. customThe resulting reaction liquid
  7. filtrationwas filtered
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V)
  11. customrecrystallized from a mixed solvent of ethanol-dichloromethane

Sources & evidence

ORD record
ord-2619162445144594b6dda9243676151b
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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