Trifluoroacetic acid → HCID 86679746, Verbindung

HRID 77459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77459
[F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:36]=[CH:35][C:22]4[N:23]([CH2:27][O:28]CC[Si](C)(C)C)[C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:28][CH2:27][N:23]1[C:22]2[CH:35]=[CH:36][C:19]([O:18][CH2:17][C:14]3[CH:13]=[N:12][C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:38])([F:1])[F:37])=[CH:5][CH:6]=4)=[N:16][CH:15]=3)=[CH:20][C:21]=2[O:25][C:24]1=[O:26]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866797456-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one

Produkt 1

HCID 86679746HCID 86679746, VerbindungAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one (0.05 g, 0.091 mmol) in DCM (3 mL) at 0° C., TFA (0.035 mL, 0.456 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. Solvent was removed under vacuum and the residue was washed with diethyl ether. The crude product was purified by preparative HPLC on an Inertsil ODS column (19×250 mm, 5μ) using 0 to 65% mobile phase B (ACN) in mobile phase A (0.1% TFA) over 6 min to give 3-(hydroxymethyl)-6-((2-((4-(trifluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)benzo[d]oxazol-2(3H)-one as a white solid (0.025 g, 61%). 1H-NMR: 400 MHz, DMSO-d6 δ ppm 5.03 (s, 2H), 5.19 (s, 2H), 6.92-6.95 (m, 1H), 7.21-7.32 (m, 4H), 7.86-7.88 (m, 1H), 8.62 (s, 2H), 9.96 (s, 1H). LCMS: R.T. 2.303 min; 449 [M+H]+.

Aufarbeitung

  1. customSolvent was removed under vacuum
  2. washthe residue was washed with diethyl ether
  3. customThe crude product was purified by preparative HPLC on an Inertsil ODS column (19×250 mm, 5μ)
  4. customover 6 min

Quellen und Nachweise

ORD-Eintrag
ord-69b1659f855f4a008f262ea7106ad62e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841301B2

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