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3-Hydroxypyridine → Oxalate

HRID 572881
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572881
I[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.CC(C)([C:29](=[O:37])CC(=O)C(C)(C)C)C.[C:39](=[O:42])([O-:41])[O-].[Cs+].[Cs+].[OH:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1>CC(C)=O.[Cu]I.CN(C)C=O>[CH3:25][N:22]1[CH2:23][CH2:24][CH:19]([O:18][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)[CH:3]=2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:20][CH2:21]1.[C:29]([O-:37])(=[O:18])[C:39]([O-:41])=[O:42]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 569474582-[(3-Iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Produkt 2

HCID 71081OxalateHCID 66835704
2-{(1-Methylpiperidin-4-yloxy)[3-(pyridin-3-yloxy)phenyl]methyl}benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A screw-capped tube is charged with 2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (example 41, 500 mg), copper(I) iodide (9 mg), 2,2,6,6-tetramethylheptane-3,5-dione (37 mg), cesium carbonate (701 mg), 3-hydroxypyridine (125 mg), powdered 4A molecular sieves (200 mg) and anhydrous N,N-dimethylformamide (1 mL). The tube is evacuated, filled with argon and sealed. After stirring at 95° C. for 2 days, the mixture is diluted with ethyl acetate, water and ammonia. After decantation, the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5). to afford the pure base that is then converted into its oxalate salt in acetone to give 2-{(1-methylpiperidin-4-yloxy)[3-(pyridin-3-yloxy)phenyl]methyl}benzothiazole, oxalate melting at 78° C.

Aufarbeitung

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with ethyl acetate, water and ammonia
  5. extractionAfter decantation, the aqueous phase is extracted with ethyl acetate
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5)
  9. customto afford the pure base that

Quellen und Nachweise

ORD-Eintrag
ord-87d063111d3d48d2b6065c69802fb903
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029357B2

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