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4-Methylmorpholine → [4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-3-methoxyphenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone

HRID 2411474
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2411474
[O:1]=[S:2]1(=[O:18])[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][C:8]=1[O:16][CH3:17].Cl.[NH:20]1[CH2:25][CH2:24][CH:23]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[O:27])[CH2:22][CH2:21]1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O>[O:18]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:20]2[CH2:25][CH2:24][CH:23]([C:26](=[O:27])[C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH2:22][CH2:21]2)=[O:13])=[CH:9][C:8]=1[O:16][CH3:17]
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Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 27408174-(4-Methylbenzoyl)piperidine hydrochlorideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 712525024-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-3-methoxybenzoic acid

Produkt 1

HCID 71252144[4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-3-methoxyphenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone
Ausbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-3-methoxybenzoic acid (285 mg) described in Preparation Example 21, (piperidin-4-yl) (p-tolyl)methanone hydrochloride (252 mg) and N-methylmorpholine (0.12 mL) was dissolved in a solution of methanol (3 mL) and water (2 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (349 mg) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (344 mg).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7f7aca35291a46b789902613538b5cb0
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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