Trifluoroacetic acid → HCID 59456972, Verbindung

HRID 1711850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711850
C([O:5][C:6](=[O:21])/[CH:7]=[CH:8]/[C:9]1[CH:20]=[N:19][C:12]2[NH:13][C:14](=[O:18])[NH:15][C:16](=[O:17])[C:11]=2[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:18]=[C:14]1[NH:13][C:12]2[N:19]=[CH:20][C:9](/[CH:8]=[CH:7]/[C:6]([OH:21])=[O:5])=[CH:10][C:11]=2[C:16](=[O:17])[NH:15]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59456936HCID 59456936, Verbindung

Produkt 1

HCID 59456972HCID 59456972, VerbindungAusbeute 116,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (E)-3-(2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)acrylic acid tert-butyl ester (379 mg, 1.19 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (2 mL). After 6 h, the solvent was concentrated, the resulting solid was treated with anhydrous HCl (10 mL of a 4 M solution in dioxane, 40 mmol) and the mixture was sonicated for 10 min. The mixture was diluted with Et2O and the solution was filtered. The olive solid was dried under high vacuum at 45° C. overnight to give the title compound (323 mg, 91%) as the TFA salt: 1H NMR (300 MHz, DMSO-d6) δ 11.89 (s, 1H), 11.56 (s, 1H), 8.94 (d, J=1.8 Hz, 1H), 8.53 (d, J=1.8 Hz, 1H), 7.69 (d, J=16.1 Hz, 1H), 6.72 (d, J=16.1 Hz, 1H), 4.40 (bs, 1H); ESI MS m/e 234 (C10H7N3O4+H)+.

Aufarbeitung

  1. concentrationthe solvent was concentrated
  2. additionthe resulting solid was treated with anhydrous HCl (10 mL of a 4 M solution in dioxane, 40 mmol) and the mixture
  3. customwas sonicated for 10 min
  4. additionThe mixture was diluted with Et2O
  5. filtrationthe solution was filtered
  6. customThe olive solid was dried under high vacuum at 45° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-03120392822e4ef5a4488754ac745228
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790709B2

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