Water → 1-(2-Fluorobenzyl)-3-[5-(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1h-pyrazol[3,4-b]pyridine

HRID 8586

Reaktionsgleichung

Reaktionsgleichung von HRID 8586
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[CH:9]=[N:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[N:15]=2)=[N:12][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH:38]([CH3:40])[CH3:39].O>CC(C)=O>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:16]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:22]2[C:14]([C:11]2[N:10]=[CH:9][C:8]([N:2]3[CH2:3][CH:4]4[CH2:7][CH:1]3[CH2:6][N:5]4[CH:38]([CH3:40])[CH3:39])=[CH:13][N:12]=2)=[N:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 219835173-[5-(2,5-Diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 219835181-(2-Fluorobenzyl)-3-[5-(5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1h-pyrazol[3,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

50 mg (0.13 mmol) of 3-[5-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (example 9) are dissolved in 5 ml of absolute acetone, and 92 mg (0.87 mmol) of sodium carbonate are added. 64 mg (0.37 mmol) of 2-iodopropane are added to the suspension, and the mixture is stirred at RT overnight. The reaction solution is mixed with water and extracted with DCM. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried and filtered. The solvent is removed in vacuo, and the residue is purified by preparative HPLC with addition of small portions of aqueous hydrochloric acid. 25 mg (42% of theory) of the product are obtained.

Aufarbeitung

  1. extractionextracted with DCM
  2. washwashed with saturated aqueous sodium chloride solution
  3. customdried
  4. filtrationfiltered
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by preparative HPLC with addition of small portions of aqueous hydrochloric acid
  7. custom25 mg (42% of theory) of the product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-3b9692a8f94a4325b9f1310600f39178
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091198B1

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