Isobutyric Acid → HCID 57725639, Verbindung

HRID 1922233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922233
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:40][NH:41][C:42](=[O:66])[C:43]1[CH:48]=[C:47]([O:49][C:50]2[CH:65]=[CH:64][C:53]3[N:54]=[C:55]([NH:57][C@H:58]4[CH2:63][CH2:62][CH2:61][NH:60][CH2:59]4)[S:56][C:52]=3[CH:51]=2)[CH:46]=[CH:45][N:44]=1>CC(N(C)C)=O>[C:1]([N:60]1[CH2:61][CH2:62][CH2:63][C@H:58]([NH:57][C:55]2[S:56][C:52]3[CH:51]=[C:50]([O:49][C:47]4[CH:46]=[CH:45][N:44]=[C:43]([C:42]([NH:41][CH3:40])=[O:66])[CH:48]=4)[CH:65]=[CH:64][C:53]=3[N:54]=2)[CH2:59]1)(=[O:6])[CH:2]([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 6590Isobutyric AcidHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57725452HCID 57725452, Verbindung

Produkt 1

HCID 57725639HCID 57725639, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To the reaction solution of isobutyric acid (4 μl, 40 μmol), HATU (15 mg, 40 μmol) and DIEA (14 μL, 80 μmol) in 400 μL of DMA was added (S)—N-methyl-4-(2-(piperidin-3-ylamino)benzo[d]thiazol-6-yloxy)picolinamide (13 mg, 30 μmol) and DIPEA (6 μL, 30 μmol). The reaction solution was stirred at room temperature for 16 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give (S)-4-(2-(1-isobutyrylpiperidin-3-ylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (6.8 mg, 15 μmol) as white powder. ES/MS m/z 454.2 (MH+).

Aufarbeitung

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1fa1a1dcea64442f828e232b41357363
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173689B2

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