Triethylamine → 1-[2-(2-Methoxy-benzylamino)-quinolin-6-yl]-3-(1-methyl-piperidin-4-yl)-urea

HRID 1803079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803079
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1.C(N(CC)CC)C.ClC(O[C:34](=[O:40])OC(Cl)(Cl)Cl)(Cl)Cl.[CH3:41][N:42]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:17][C:34]([NH:48][CH:45]3[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]3)=[O:40])[CH:13]=2)[N:8]=1

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 27375314-Amino-1-methylpiperidineHCID 43450845N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

Produkt 1

HCID 442051781-[2-(2-Methoxy-benzylamino)-quinolin-6-yl]-3-(1-methyl-piperidin-4-yl)-ureaAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 65 mg, 0.233 mmol) was dissolved in tetrahydrofuran (3 ml) and triethylamine (0.052 mL, 0.512 mmol) was added. At 0° C. bis(trichloromethyl)carbonate (31 mg, 0.105 mmol) was added and the reaction mixture subsequently heated to 80° C. for 3 h. Upon cooling to ambient temperature triethylamine (0.052 mL, 0.512 mmol) and 1-methyl-piperidin-4-ylamine (27 mg, 0.233 mmol) were added and the whole reaction mixture was stirred over night at 50° C. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and the filtrate was evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol) and to yield the title compound as white solid (15 mg, 15%). MS: m/e=420.4 (M+H+).

Aufarbeitung

  1. additionwere added
  2. customthe whole reaction mixture
  3. customAfter evaporation of the solvent
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried on sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-3b416c757c654f968de59f4e67909983
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350028B2

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