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Trifluoroacetic acid → 1-(4-(1-(2-methoxyethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamine

HRID 1509288
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Reaktionsgleichung

Reaktionsgleichung von HRID 1509288
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:15]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5([NH:34]C(=O)OC(C)(C)C)[CH2:33][CH2:32][CH2:31]5)=[CH:26][CH:25]=4)=[N:14][C:11]=3[O:12][CH2:13][C:8]2=[N:7][N:6]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:15]([C:24]4[CH:25]=[CH:26][C:27]([C:30]5([NH2:34])[CH2:31][CH2:32][CH2:33]5)=[CH:28][CH:29]=4)=[N:14][C:11]=3[O:12][CH2:13][C:8]2=[N:7][N:6]=1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86683657Tert-butyl (1-(4-(1-(2-methoxyethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate

Produkt 1

HCID 532626721-(4-(1-(2-methoxyethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutanamineAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

Tert-butyl (1-(4-(1-(2-methoxyethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (12 mg, 0.022 mmol) was dissolved in dichloromethane (0.5 ml); TFA (0.5 ml) was added at room temperature and the resulting mixture was stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜2 ml) and concentrated to dryness under reduced pressure. This was repeated three times. The residue was then slurred in diethyl ether (2 ml) and after settling the supernatant solvent was removed by pipette. This was repeated three times. The residue was then slurred in n-hexane (2 ml) and after settling the supernatant solvent was removed by pipette. This was repeated three times. The remaining solvent was removed under reduced pressure and dried to give the desired product as an off-white solid (5 mg, 50% yield). LCMS (Method D) RT=0.741 min, M+1=454. 1H-NMR (500 MHz, CD3OD) δ 8.40 (1H, s), 7.52-7.47 (2H, d), 7.46-7.41 (2H, d), 7.38-7.34 (3H, m), 7.32-7.26 (2H, dd), 5.65 (2H, s), 3.94 (2H, t), 3.49 (2H, t), 3.35 (3H, s), 2.82-2.74 (2H, m), 2.63-2.54 (2H, m), 2.30-2.19 (1H, m), 2.04-1.93 (1H, m).

Aufarbeitung

  1. concentrationThe solution was immediately concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether (˜2 ml)
  3. concentrationconcentrated to dryness under reduced pressure
  4. customwas removed by pipette
  5. customwas removed by pipette
  6. customThe remaining solvent was removed under reduced pressure
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6e54a9dfb5fa4ab8a07f9839cbc85e45
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221838B2

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