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Potassium Carbonate → 2-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethylamine

HRID 1685793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1685793
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH2:25][CH3:26])[CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:27])[CH2:4][CH3:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].C([NH:41][CH2:42][CH2:43]Br)(OC(C)(C)C)=O>C(#N)C>[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:43][CH2:42][NH2:41])=[C:19]([CH2:25][CH3:26])[CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:27])[CH2:4][CH3:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 1363773324-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol

Produkt 1

HCID 672656372-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethylamineAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (700 mg, 1.82 mmol) and K2CO3 (760 mg, 5.45 mmol) in acetonitrile (14 mL), 2-(Boc-amino)-ethylbromide (839 mg, 3.63 mmol) is added. The mixture is stirred at 80° C. for 12 h. The mixture is filtered and the filtrate is concentrated. The residue is dissolved in DCM (10 mL) and treated with TFA (1.4 mL). The mixture is stirred at rt for 19 h before another portion of TFA (0.7 mL) is added. Stirring is continued at rt for another 21 h. The mixture is diluted with DCM and washed with 1 M aq. NaOH. The washing is extracted back with DCM. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC. The product containing fractions are combined, concentrated, dissolved in methanol:water 9:1 and filtered over Amberlyst A-21. The filtrate is evaporated and dried to give the title compound (513 mg) as a pale yellow resin; LC-MS: tR=0.44 min; [M+1]+=429.20; 1H NMR (D6-DMSO): δ1.03 (t, J=7.0 Hz, 6H), 1.23 (t, J=7.5 Hz, 3H), 2.22 (s, 3H), 2.35 (s, 3H), 2.58 (q, J=7.3 Hz, 4H), 2.73 (q, J=7.5 Hz, 2H), 3.05 (t, J=5.5 Hz, 2H), 3.73 (s, 3H), 3.86 (t, J=5.5 Hz, 2H), 7.75 (s, 2H), 7.80 (s, 1H).

Aufarbeitung

  1. additionis added
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. dissolutionThe residue is dissolved in DCM (10 mL)
  5. additiontreated with TFA (1.4 mL)
  6. stirringThe mixture is stirred at rt for 19 h before another portion of TFA (0.7 mL)
  7. additionis added
  8. stirringStirring
  9. waitis continued at rt for another 21 h
  10. additionThe mixture is diluted with DCM
  11. washwashed with 1 M aq. NaOH
  12. extractionThe washing is extracted back with DCM
  13. dry with materialThe combined organic extracts are dried over MgSO4
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe crude product is purified by prep
  17. additionThe product containing fractions
  18. concentrationconcentrated
  19. dissolutiondissolved in methanol:water 9:1
  20. filtrationfiltered over Amberlyst A-21
  21. customThe filtrate is evaporated
  22. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4aa22b4d06464d98a605663d19a76eb5
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148410B2

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