Acetic Acid → HCID 66803171, Verbindung

HRID 341448

Reaktionsgleichung

Reaktionsgleichung von HRID 341448
[NH:1]1[CH2:4][CH:3]([C:5]2[O:9][N:8]=[C:7]([C:10]3[N:15]=[C:14]([N:16]([CH3:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:13]=[C:12]([NH2:24])[N:11]=3)[N:6]=2)[CH2:2]1.FC(F)(F)[CH2:27][CH:28]=[O:29].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH2:24][C:12]1[N:13]=[C:14]([N:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[C:10]([C:7]2[N:6]=[C:5]([CH:3]3[CH2:2][N:1]([C:28](=[O:29])[CH3:27])[CH2:4]3)[O:9][N:8]=2)[N:11]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5049666Sodium triacetoxyborohydrideHCID 66803027HCID 66803027, Verbindung2×

Produkt 1

HCID 66803171HCID 66803171, VerbindungAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

6-[5-(Azetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamine (Intermediate 149, 85 mg, 0.26 mmol), 3,3,3-trifluoropropanal (32 μL, 0.28 mmol) and acetic acid (45 μL, 0.78 mmol) were combined in DCE (5 mL) and stirred for 3 h at room temperature. Sodium triacetoxyborohydride (83 mg, 0.39 mmol) was added and the mixture was heated to 70 C for 5 h. The reaction mixture was cooled at room temperature, concentrated under vacuum and purified by preparative HPLC, Method C, to afford the title compound as a white solid (25 mg, 26%).

Aufarbeitung

  1. temperaturethe mixture was heated to 70 C for 5 h
  2. temperatureThe reaction mixture was cooled at room temperature
  3. concentrationconcentrated under vacuum
  4. custompurified by preparative HPLC, Method C

Quellen und Nachweise

ORD-Eintrag
ord-5204d0a50fa04cde863f23d2d4153df8
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895733B2

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