Trifluoroacetic acid → HCID 71143541, Verbindung

HRID 2363274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363274
[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[N:31](COCC[Si](C)(C)C)[CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:7][N:6]([C:8]2[CH:19]=[CH:18][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:5]1)#[N:2].FC(F)(F)C(O)=O>>[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[NH:31][CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:18][CH:19]=2)[CH2:7]1)#[N:2]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71143552HCID 71143552, Verbindung

Produkt 1

HCID 71143541HCID 71143541, Verbindung

Versuchsvorschrift

4-{3-(Cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylbenzamide was dissolved in dichloromethylene (5 mL). To the solution was added trifluoroacetic acid (TFA) (2.5 mL). The mixture was stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure. The residue was dissolved in methanol (10 mL). To the solution was added ethylenediamine (1 mL). The mixture was stirred at room temperature for 4 hours, and was purified by RP-HPLC (pH=10) to afford the desired product (0.415 g). LCMS (M+H)+: m/z=440.1. The high purity (99.6%) of the product was obtained by re-crystallization from acetone-ether, 1H NMR (400 MHz, CDCl3): δ 9.57 (s, 1H), 8.31 (d, J=4.9 Hz, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70 (m, 2H), 7.39 (d, J=3.4 Hz, 1H), 7.18 (d, J=4.9 Hz, 1H), 6.70 (d, J=3.4 Hz, 1H), 6.55 (m, 2H), 5.79 (d, J=7.8 Hz, 1H), 4.47 (d, J=8.3 Hz, 2H), 4.38 (d, J=8.3 Hz, 2H), 4.27 (m, 1H), 3.45 (s, 2H), 1.25 (d, J=6.7 Hz, 6H).

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. additionTo the solution was added ethylenediamine (1 mL)
  4. stirringThe mixture was stirred at room temperature for 4 hours
  5. customwas purified by RP-HPLC (pH=10)

Quellen und Nachweise

ORD-Eintrag
ord-0e36013e2abc4fd790ee6536b425ea38
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691807B2

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