Triethylamine → HCID 57780718, Verbindung

HRID 2076101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076101
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19](OS(C)(=O)=O)[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 57780691HCID 57780691, Verbindung

Produkt 1

HCID 57780718HCID 57780718, VerbindungAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of methanesulfonic acid 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-5,6,7,8-tetrahydro-quinazolin-8-yl ester (61 mg, 0.14 mmol) in tetrahydrofurane (1.4 mL) was added under nitrogen at 0° C. pyrrolidine (20 mg, 0.28 mmol) and triethyl amine (29 mg, 0.28 mmol). The reaction was stirred at room temperature over night, heated to reflux for 2 hours. A few drops of dimethylformamide were added and the reaction was stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure, dissolved in water and extracted twice with ethyl acetate. The combined organic layers were washed with dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane/methanol/concentrated aqueous ammonia (19:1:0.2 v/v/v) as eluent to yield the title compound (24 mg, 42%) as a yellow solid. MS ISP (m/e): 234.3 (100), 334 (24), 405.3 (69) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.61 (s, 1H), 8.29 (s, 1H), 7.95 (s, 1H), 7.64 (s, 1H), 7.38 (d, 1H), 7.20 (d, 1H), 7.02 (s, 1H), 3.80 (s, 3H), 2.55-2.80 (m, 4H), 2.14 (s, 3H), 2.04 (m, 2H), 1.60-1.80 (m, 6H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. stirringthe reaction was stirred at room temperature for 2 hours
  4. concentrationThe reaction was concentrated under reduced pressure
  5. dissolutiondissolved in water
  6. extractionextracted twice with ethyl acetate
  7. washThe combined organic layers were washed
  8. dry with materialwith dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2111b946c97d4811b61546745c32718f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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