Water → HCID 21897401, Verbindung

HRID 719501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719501
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([O:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:16]2[CH:15]=[N:14]1.Cl[C:30]1[N:35]=[C:34]([N:36]([CH3:38])[CH3:37])[CH:33]=[C:32](C)[N:31]=1.[C:40]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:10])=[O:11])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([O:22][CH:23]3[CH2:24][CH2:25][N:26]([C:30]4[N:35]=[C:34]([N:36]([CH3:38])[CH3:37])[C:33]([CH3:40])=[CH:32][N:31]=4)[CH2:27][CH2:28]3)=[C:16]2[CH:15]=[N:14]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10813CrimidineHCID 11430Potassium CarbonateHCID 218977401-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

Produkt 1

HCID 21897401HCID 21897401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine HCl salt (0.3 g, 0.97 mmol) and (2-chloro-6-methyl-pyrimidin-4-yl)-dimethyl-amine (285 mg, 0.97 mmol) were dissolved in DMF (10 mL). The solution was treated with K2CO3 (398 mg, 2.91 mmol) at an ambient temperature. After stirring at 65° C. for five hours, the reaction was poured into H2O (20 mL). The organic compound was extracted with ethyl acetate (30 mL) and washed with brine. The ethyl acetate layer was dried over MgSO4 and concentrated under vacuum. The residue was purified over SiO2 to afford Compound A212 (312 mg, 65.2%). 1H NMR (400 Mz, DMSO-d6) δ 8.69 (s, 1H), 8.64 (s, 1H), 8.17 (dd, J=8.4, 1.8, 1H), 8.08 (d, J=4.2, 1H), 8.01 (dd, J=8.4, 1.8, 1H), 7.72 (s, 1H), 5.65 (m, 1H), 4.23˜4.20 (m, 2H), 3.50˜3.46 (m, 2H), 3.39 (s, 3H), 3.00 (s, 6H), 2.13 (s, 3H), 2.10˜2.09 (m, 2H), 1.77˜1.72 (m, 2H), LCMS 527.5[M+1].

Aufarbeitung

  1. extractionThe organic compound was extracted with ethyl acetate (30 mL)
  2. washwashed with brine
  3. dry with materialThe ethyl acetate layer was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified over SiO2
  6. customto afford Compound A212 (312 mg, 65.2%)

Quellen und Nachweise

ORD-Eintrag
ord-3dc24e842a6942518b47061138701367
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132426B2

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