Trifluoroacetic acid → 1-(Piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol

HRID 410518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410518
[OH:1][C:2]([CH:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]1)([C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:10]=2)=[CH:7][N:8]=1)[CH3:3].C(O)(C(F)(F)F)=O>ClCCl>[NH:29]1[CH2:30][CH2:31][CH:26]([C:2]([C:4]2[S:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]4[N:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[CH:18][N:17]=4)[CH:10]=3)=[CH:7][N:8]=2)([OH:1])[CH3:3])[CH2:27][CH2:28]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 67431059Tert-butyl 4-{1-hydroxy-1-[5-(3-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}piperidine-1-carboxylate

Produkt 1

HCID 672566901-(Piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanolAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the product of Step 4 (18.2 mg, 0.033 mmol) in dichloromethane (1 mL) was added TFA (1.00 mL, 12.98 mmol) and the mixture was stirred at room temperature. The solvent was removed by evaporation and stripped with ethyl acetate. The residue was concentrated and dried under high-vacuum to afford 1-(piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol (Example 15(2), 12.5 mg, 0.018 mmol) as a TFA salt. APCI: [M+H]+ m/z 450.1. 1H NMR (500 MHz, DMSO-d6): δ 10.34 (1H, s), 8.86 (1H, d, J=4.89 Hz), 8.43 (2H, broad s), 8.14 (1H, s), 8.01 (1H, s), 7.67 (1H, d, J=8.10 Hz), 7.39 (1H, t, 7.88 Hz), 7.34-7.29 (2H, m), 3.18-3.02 (2H, m), 2.61-2.54 (2H, m), 1.92-1.77 (2H, m), 1.51 (3H, s), 1.55-1.41 (1H, m), 1.38-1.22 (1H, m). rhSYK activity=+++

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. concentrationThe residue was concentrated
  3. customdried under high-vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c077f76af17a435198ecb18342350499
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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