2-(5-Amino-1,3-dihydro-2H-isoindol-2-yl)acetamide → 2-{5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-isoindol-2-yl}-acetamide

HRID 1262150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262150
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]2)=[CH:11][CH:10]=1.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[CH2:32][N:31]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:30]2>COC(O)CC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[CH2:32][N:31]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:30]4)=[N:16]2)=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 574160552-(5-Amino-1,3-dihydro-2H-isoindol-2-yl)acetamideHCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Produkt 1

HCID 667121882-{5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-isoindol-2-yl}-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3032390Propylene glycol methyl etherLösungsmittel

Versuchsvorschrift

Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.111 g, 0.298 mmol) and 2-(5-Amino-1,3-dihydro-isoindol-2-yl)-acetamide (0.077 g, 0.40 mmol) were reacted in an analogous manner to Example 908D at 50° C. for 16 h in methoxypropanol. Pale yellow solid was filtered off, washed with water. Found to be pure product (35 mg, 28%). LCMS=414.9 (M+H), HPLC rt=2.256 min, purity=99%. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.40 (s, 1H), 8.95 (s, 1H), 7.78 (d, J=7.4 Hz, 1H), 7.75 (s, 1H), 7.47 (dd, J=7.6 Hz, 1H), 7.39 (d, J=8.6 Hz, 1H), 7.32 (s, 1H), 7.21 (d, J=8.6 Hz, 1H), 7.13-7.05 (m, 3H), 6.94 (d, J=4.6 Hz, 1H), 6.90 (d, J=4.6 Hz, 1H), 3.89 (s, 4H0, 3.78 (s, 3H), 3.27 (s, 2H).

Aufarbeitung

  1. filtrationPale yellow solid was filtered off
  2. washwashed with water
  3. customLCMS=414.9 (M+H), HPLC rt=2.256 min, purity=99%

Quellen und Nachweise

ORD-Eintrag
ord-34a60d3ef9c3481db657413df6df6d9e
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

Notizen zur Reaktion

Wird geladen…