Triethylamine → HCID 46897183, compound

HRID 1808366Notes

Reaction equation

HRID 1808366 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([S:11]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][C:25]([N:27]4[CH2:36][CH2:35][C:30]5([CH2:34][NH:33][CH2:32][CH2:31]5)[CH2:29][CH2:28]4)=[O:26])[CH:22]=3)[CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[C:6]([CH3:37])[CH:5]=1.[Cl-].Cl[C:40]1[CH:45]=[CH:44][NH+:43]=[CH:42][CH:41]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)CCC.C(OCC)(=O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH3:37])[C:7]([S:11]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][C:25]([N:27]4[CH2:28][CH2:29][C:30]5([CH2:34][N:33]([C:40]6[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=6)[CH2:32][CH2:31]5)[CH2:35][CH2:36]4)=[O:26])[CH:22]=3)[CH2:17][CH2:16][CH2:15]2)(=[O:12])=[O:13])=[C:8]([CH3:10])[CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 108772907379-35-3HCID 685056272-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)-1-(2,8-diazaspiro[4.5]decan-8-yl)ethanone hydrochloride

Product 1

HCID 46897183HCID 46897183, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)-1-(2,8-diazaspiro[4.5]decan-8-yl)ethanone hydrochloride (0.15 g, 0.274 mmol), 4-chloropyridinium chloride (0.12 g, 0.821 mmol) and triethylamine (0.15 ml, 1.09 mmol) was refluxed for 15 h in 1-butanol (7 ml). Saturated sodium hydrogen carbonate solution (20 ml) and ethyl acetate (50 ml) were then added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (20 ml), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/-methanol/ammonia (25% aq.), 300:100:50:1) and the desired exemplary compound G-09 was obtained. Yield: 0.1 g (62%). MS, Rt=3.3 min; m/z=589.1 [MH]+

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic phases were washed with saturated sodium chloride solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/-methanol/ammonia (25% aq.), 300:100:50:1)
  7. customwas obtained

Sources & evidence

ORD record
ord-4cbac5e354c5454b94ceaec6ef1ad69b
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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