Trifluoroacetic acid → HCID 178460032, Verbindung

HRID 577690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577690
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][N:19]4COCC[Si](C)(C)C)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][NH:19]4)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86679632HCID 86679632, Verbindung

Produkt 1

HCID 178460032HCID 178460032, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of N-{3-[(2-{[1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl]amino}-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purin-6-yl)oxy]phenyl}prop-2-enamide (271 mg, 0.471 mmol) in DCM (5.89 mL) was added TFA (1.81 mL, 23.6 mmol). The resulting solution was stirred at rt overnight, then concentrated and dried under vacuum. The resulting residue was taken up in water and neutralized with NaHCO3 to get a slightly sticky suspension. The solid was filtered off, washed with water, dried, and collected to give the crude product, which was purified by SFC to afford the title compound (21 mg, 10 yield) as a lyophilized solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.80 (br. s., 1H) 10.37 (br. s., 1H) 9.20 (br. s., 1H) 8.01-8.11 (m, 1H) 7.61-7.78 (m, 1H) 7.48 (br. s., 1H) 7.37 (d, J=6.32 Hz, 1H) 7.03 (d, J=7.33 Hz, 2H) 6.36-6.59 (m, 1H) 6.20-6.34 (m, 1H) 5.77 (dd, J=10.23, 1.89 Hz, 1H) 4.57 (br. s., 1H) 3.99-4.27 (m, 1H) 3.65-3.94 (m, 3H) 3.00 (br. s., 2H) 2.79 (m, J=15.66 Hz, 1H) 2.00 (br. s., 1H) 1.23 (s, 1H). m/z (APCI+) for C22H23N9O2 446.05 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customto get a slightly sticky suspension
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customcollected
  8. customto give the crude product, which
  9. customwas purified by SFC

Quellen und Nachweise

ORD-Eintrag
ord-f17d8639c0a248ba8eed55692627ffa0
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040547B2

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