N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine → 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine

HRID 1520206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520206
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)[S:16][C:17]=3[F:18])[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[F:18][C:17]1[S:16][C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)=[N:14][C:13]=1[C:11]1[CH:12]=[N:8][NH:9][CH:10]=1

Komponenten

3

Edukt 1

HCID 86658559N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine

Produkt 1

HCID 468367265-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

According to Scheme 6 Step 4: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine (0.24 mmol, 95 mg) in TFA (3 mL) was microwaved for 8 minutes at 140° C. After evaporation of the solvent, the reaction mixture was neutralized with a solution of NaOH (1 M). The aqueous phase was extracted with DCM and with AcOEt. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was washed with Et2O to yield 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine (0.12 mmol, 33 mg, 50%) as a beige solid.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous phase was extracted with DCM and with AcOEt
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. washThe resulting crude product was washed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-c3592a2b046e4334a3a4958cc275bd32
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073907B2

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