Trifluoroacetic acid → N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine

HRID 63361

Reaktionsgleichung

Reaktionsgleichung von HRID 63361
C(O)(C(F)(F)F)=O.[CH2:8]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([CH2:23][O:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([NH:35]C(=O)OC(C)(C)C)=[CH:27][CH:26]=3)[CH:20]=[CH:19][N:18]=2)[CH:13]=[N:12][CH:11]=1)[CH3:9]>C(Cl)Cl>[NH2:35][C:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([O:24][CH2:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]3[CH:13]=[N:12][CH:11]=[C:10]([CH2:8][CH3:9])[N:15]=3)[CH:22]=2)=[CH:26][CH:27]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 118317293Tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate2×

Produkt 1

HCID 118305959N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amineAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (1.485 mL, 19.09 mmol) was added to a solution of tert-butyl (4-((2-((6-ethylpyrazin-2-yl)amino)pyridin-4-yl)methoxy)naphthalen-1-yl)carbamate (Intermediate D (protected)) (360 mg, 0.763 mmol) in DCM (15 mL), and the reaction mixture stirred at room temperature for 4 h, then concentrated in vacuo. The residue was combined with sat. sodium hydrogencarbonate solution and stirred at room temperature for 16 h. The solid was filtered, washing with acetonitrile, and dried under vacuum to give the subtitle compound N-(4-(((4-aminonaphthalen-1-yl)oxy)methyl)pyridin-2-yl)-6-ethylpyrazin-2-amine as a beige solid (200 mg, 69%); Rt 2.14 min (Method 2); m/z 372 (M+H)+ (ES+); 1H NMR δ: 1.20 (3H, t), 2.64 (2H, q), 5.18-5.24 (4H, overlapping m), 6.59 (1H, d), 6.82 (1H, d), 7.03 (1H, d), 7.41-7.51 (2H, overlapping m), 7.98-8.01 (2H, m), 8.04 (1H, m), 8.22-8.29 (2H, overlapping m), 8.91 (1H, s), 10.04 (1H, s).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. stirringstirred at room temperature for 16 h
  3. filtrationThe solid was filtered
  4. washwashing with acetonitrile
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-291dceeaa8ca472d938abcb908bbdb3a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447076B2

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