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Trifluoroacetic acid → 4-{3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamide

HRID 2363315
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2363315
[C:1]([CH2:3][C:4]1([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][N:35](COCC[Si](C)(C)C)[C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:7][N:6]([C:8]2[C:21]([F:22])=[CH:20][C:11]([C:12]([NH:14][C@@H:15]([CH:17]3[CH2:19][CH2:18]3)[CH3:16])=[O:13])=[C:10]([F:23])[CH:9]=2)[CH2:5]1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([CH2:3][C:4]1([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][NH:35][C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:7][N:6]([C:8]2[C:21]([F:22])=[CH:20][C:11]([C:12]([NH:14][C@@H:15]([CH:17]3[CH2:18][CH2:19]3)[CH3:16])=[O:13])=[C:10]([F:23])[CH:9]=2)[CH2:5]1)#[N:2]
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 712079354-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamide

Produkt 1

HCID 711557114-{3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamideAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

4-{3-(Cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamide (0.48 g) was dissolved in a solution of trifluoroacetic acid (3 mL, 40 mmol) in methylene chloride (3 mL). The solution was stirred at room temperature for 1.5 hours. It was concentrated under reduced pressure. The residue was dissolved in methanol (5 mL). To the solution was added ethylenediamine (3 mL). The mixture was stirred at room temperature for 2 hours. After concentration the crude material was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-10%) to afford the desired product (245 mg, 24%). LCMS (M+H)+: m/z=503.2. 1H NMR (400 MHz, DMSO-d6): δ 12.60 (s, 1H), 9.08 (s, 1H), 8.85 (s, 1H), 8.57 (s, 1H), 7.84 (dd, J=8.0, 4.0 Hz, 1H), 7.78 (m, 1H), 7.36 (dd, J=13.0, 7.0 Hz, 1H), 7.23 (m, 1H), 6.64 (dd, J=13.0, 7.0 Hz, 1H), 4.70 (d, J=8.0 Hz, 2H), 4.45 (d, J=8.0 Hz, 2H), 3.78 (s, 2H), 3.43 (m, 1H), 1.09 (d, J=6.5 Hz, 6H), 0.97 (m, 1H), 0.43 (m, 1H), 0.37 (m, 1H), 0.28 (m, 1H), 0.19 (m, 1H).

Aufarbeitung

  1. concentrationIt was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (5 mL)
  3. additionTo the solution was added ethylenediamine (3 mL)
  4. stirringThe mixture was stirred at room temperature for 2 hours
  5. concentrationAfter concentration the crude material
  6. customwas purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-41e8f5bcb70a4d93bca39f3188f6d9ec
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691807B2

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