N-(2-aminoethyl)acetamide → N-(2-(6-(Cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide

HRID 1620305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620305
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)[CH:8]=2)[N:3]=1.[NH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24]>C1COCC1>[CH:16]1([CH2:15][O:14][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])[C:11]([CH:12]=[O:13])=[CH:10]3)[CH2:18][CH2:17]1

Komponenten

4

Edukt 2

HCID 66082N-(2-aminoethyl)acetamideHCID 866698362-Chloro-6-(cyclopropylmethoxy)quinoline-3-carbaldehyde2×

Produkt 1

HCID 86669837N-(2-(6-(Cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a stirred solution of 2-chloro-6-(cyclopropylmethoxy)quinoline-3-carbaldehyde SLA 47086 (770 mg, 2.94 mmol) in THF (15 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added N-(2-aminoethyl)acetamide (1.202 g, 11.8 mmol) and the reaction mixture was stirred for 6 h at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 20 min at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with a 10 N aqueous NaOH solution. THF was then evaporated before extraction with CH2Cl2 (100 mL). The separated organic layer was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum to give N-(2-(6-(cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide SLA 47092 as a yellow solid (365 mg, 38% yield).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. additionthe resulting yellow oil was taken up in a mixture of THF
  4. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 20 min at RT
  5. customThe volatiles were then removed at 40° C. under vacuum
  6. customTHF was then evaporated before extraction with CH2Cl2 (100 mL)
  7. washThe separated organic layer was washed with brine (20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cffaf4c585ad4a39b2b91677652f6cd7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772316B2

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