Dimethylformamide → {4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(4-trifluoromethoxy-phenyl)-methanone

HRID 719496

Reaktionsgleichung

Reaktionsgleichung von HRID 719496
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[C:15]2[CH:14]=[N:13]1.C(N(CC)CC)C.[F:35][C:36]([F:48])([F:47])[O:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1C(Cl)=O.CN([CH:52]=[O:53])C>>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]3[CH2:23][CH2:24][N:25]([C:52]([C:44]4[CH:43]=[CH:39][C:38]([O:37][C:36]([F:35])([F:47])[F:48])=[CH:46][CH:45]=4)=[O:53])[CH2:26][CH2:27]3)=[C:15]2[CH:14]=[N:13]1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27772412-(Trifluoromethoxy)benzoyl ChlorideHCID 218975531-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 21897805{4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(4-trifluoromethoxy-phenyl)-methanone

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 50 mL round-bottomed flask was placed 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (300 mg, 0.7 mmol) and triethylamine (584 μl). DMF (6 mL) was added to completely dissolve the solid material. The reaction flask was immersed in an ice-bath. Trifluoromethoxybenzoyl chloride (180 mg, 0.8 mmol) was added to the solution and the mixture was stirred 2 h under N2 at 0° C. After all of the starting amine was completely converted as indicated by LCMS, the reaction was stopped by quenching with water. The reaction mixture was then concentrated under vacuum and purified by preparative HPLC. 1H NMR (CDCl3, 400 MHz) δ 1.98 (m, 1H), 2.12 (m, 2H), 2.27 (m, 1H), 3.13 (s, 3H), 3.51 (m, 1H), 3.79 (m, 2H), 4.21 (m, 1H), 5.76 (m, 1H), 7.31 (d, 2H), 7.52 (d, 2H), 7.95 (m, 3H), 8.36 (s, 1H), 8.65 (s, 1H). Exact mass calculated for C25H21F4N5S 579.12, found 580.2 (MH+).

Aufarbeitung

  1. customIn a 50 mL round-bottomed flask was placed
  2. dissolutionto completely dissolve the solid material
  3. customThe reaction flask was immersed in an ice-bath
  4. customby quenching with water
  5. concentrationThe reaction mixture was then concentrated under vacuum
  6. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2c3f89c64b2848088a5a65422363e3b0
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132426B2

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