Dimethylformamide → HCID 56945615, Verbindung

HRID 1262129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262129
[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:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:21][C:20]=3[O:31][CH3:32])=[N:16]2)=[CH:11][CH:10]=1.C(OC([NH:40][C:41]([CH3:46])([CH3:45])[C:42](O)=[O:43])=O)(C)(C)C.Cl.CN(C)CCCN=C=NCC.CN(C)C=O>C([O-])(O)=O.[Na+]>[NH2:40][C:41]([CH3:46])([CH3:45])[C:42]([N:28]1[CH2:29][CH2:30][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:15]3[N:14]=[CH:13][C:12]4=[CH:11][CH:10]=[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])[N:17]4[N:16]=3)=[C:20]([O:31][CH3:32])[CH:21]=2)[CH2:26][CH2:27]1)=[O:43]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 66711490HCID 66711490, Verbindung

Produkt 1

HCID 56945615HCID 56945615, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methoxy-4-piperidin-4-yl-phenyl)-amine (80.00 mg, 0.186 mmol), 2-tert-butoxycarbonylamino-2-methyl-propionic acid (0.045 g, 0.22 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.043 g, 0.22 mmol) and N,N-dimethylformamide (1.54 mL, 20.0 mmol) were combined in a round-bottom flask and stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous NaHCO3 and the resulting precipitate was collected by filtration and was washed twice with water, then dried under vacuum and used in the next step without further purification. Following the experimental procedure described in Example 787b), this precipitate was converted to 2-amino-1-(4-{3-methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-2-methyl-propan-1-one as a yellow solid (58 mg, 61%). MP: 81-89° C.; 1H-NMR (CDCl3) δ 8.69 (s, 1H), 8.30 (d, J=8.8 Hz, 1H), 7.99 (dd, J=7.6; 1.6 Hz, 1H), 7.44 (m, 2H), 7.13 (m, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.02 (d, J=4.7 Hz, 1H), 6.83 (d, J=4.7 Hz, 1H), 6.70 (m, 2H), 4.84 (m, 2H), 3.89 (s, 3H), 3.84 (s, 3H), 2.88 (m, 2H), 2.72 (m, 1H), 1.90 (m, 2H), 1.63 (m, 4H), 1.45 (s, 6H); LC/MS (ESI+): 515.0 (M+H).

Aufarbeitung

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwas washed twice with water
  3. customdried under vacuum
  4. customused in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a2417a34feca4a729e96e2a6a10a706f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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