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1-Hydroxybenzotriazole → [4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone

HRID 2411466
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Reaktionsgleichung

Reaktionsgleichung von HRID 2411466
[O:1]=[S:2]1(=[O:16])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[O:25])[CH2:20][CH2:19]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[O:16]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]([C:11]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](=[O:25])[C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[CH2:20][CH2:19]2)=[O:13])=[CH:14][CH:15]=1
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Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27408174-(4-Methylbenzoyl)piperidine hydrochlorideHCID 66250114-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acid

Produkt 1

HCID 71261250
[4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone
Ausbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-(1,1-Dioxo-1λ6-isothiazolidin-2-yl)benzoic acid (253 mg) described in Preparation Example 16, (piperidin-4-yl) (p-tolyl)methanone hydrochloride (252 mg), 1-hydroxybenzotriazole 1 hydrate (142 mg) and triethylamine (0.15 mL) were dissolved in N,N-dimethylformamide (5 mL), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (202 mg) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (108 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-54dcd11727aa4ebba5b8a60c12deff2f
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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