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Water → N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamine

HRID 63798
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 63798
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:16]3=[CH:25][C:26]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:27][N:15]3[N:14]=2)[CH:8]=1)(=O)=O.[CH3:32][S:33]([O-:35])=[O:34].[Na+].O>CN1CCCC1=O>[CH3:31][N:29]([CH3:30])[CH2:28][C:26]1[CH:25]=[C:16]2[N:15]([CH:27]=1)[N:14]=[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][S:33]([CH3:32])(=[O:35])=[O:34])[CH:8]=1)[N:18]=[C:17]2[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 117988030HCID 117988030, Verbindung

Produkt 1

HCID 72201093N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

Compound 19 (45 mg, 0.1 mmol) and sodium methylsulfinate (41 mg, 0.4 mmol) were dissolved in 2 mL N-methylpyrrolidone. The mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts. After completion of the reaction, the reaction mixture was poured into water, extracted for three times with ethyl acetate, and extracted for three times with dichloromethane. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to a small volume. The crude product was purified by a preparative plate (dichloromethane:methanol=6:1) to obtain 12 mg of white solid (28.0%). m.p. 143-144° C. 1H NMR (300 MHz, CDCl3): δ 8.32 (d, J=5.2 Hz, 1H), 8.29 (s, 1H), 7.63 (d, J=1.2 Hz, 1H), 7.50 (d, J=5.2 Hz, 2H), 6.78 (d, J=1.2 Hz, 1H), 4.34 (s, 2H), 4.11 (t, J=4.4 Hz, 4H), 3.88 (t, J=4.4 Hz, 4H), 3.66 (s, 2H), 2.78 (s, 3H), 2.36 (s, 6H). MS (EI) m/e (%): 429 (M+, 12).

Aufarbeitung

  1. customThe mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts
  2. customAfter completion of the reaction
  3. extractionextracted for three times with ethyl acetate
  4. extractionextracted for three times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure to a small volume
  7. customThe crude product was purified by a preparative plate (dichloromethane:methanol=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-2366236a36d94abc91175c5debdc09b4
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447101B2

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