Formaldehyde → 1-[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanol

HRID 1094863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094863
[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH:11]([OH:13])[CH3:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[CH2:14]=O.O.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CC(O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH:11]([OH:13])[CH3:12])=[C:10]([CH2:14][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:6]2[N:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 962WaterHCID 8083MorpholineHCID 552977291-{4-Aminopyrrolo[2,1-f][1,2,4]triazin-6-yl}ethan-1-ol

Produkt 1

HCID 579552741-[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanolAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of AcOH (70 mL) was added 1-(4-aminopyrrolo[2,1-f][1,2,4]triazin-6-yl)ethanol (611 mg, 3.43 mmol) followed by the addition of a 0.5 M solution of 37% formaldehyde in water (0.26 mL, 3.43 mmol) and morpholine (0.30 mL, 3.43 mmol) in AcOH (6.86 mL) was added. The reaction was heated to 60° C. for 1.5 h. The solution was allowed to cool to rt and was then evaporated via rotary evaporation chasing the remaining AcOH with toluene. The crude material was purified by column chromatography (85:15 v/v CH2Cl2-EtOAc) to afford 633 mg of the above compound (2.28 mmol, yield 67%). 1H-NMR (DMSO-d6) δ 7.79 (s, 1H), 7.57 (br s, 2H), 6.85 (s, 1H), 4.94 (m, 1H), 3.84 (m, 2H), 3.49 (m, 4H), 2.37 (m, 4H), 1.41 (d, J=6.6 Hz, 3H); MS [M+H]+=278.0; LCMS RT=1.01 min.

Aufarbeitung

  1. additionwas added
  2. temperatureto cool to rt
  3. customwas then evaporated via rotary evaporation
  4. customThe crude material was purified by column chromatography (85:15 v/v CH2Cl2-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-ea0176e86bfd465db011dd7ec7fba5c8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133995B2

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