Isopropyl chloroformate → {4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(5-morpholin-4-ylmethyl-furan-2-yl)-methanone

HRID 719510

Reaktionsgleichung

Reaktionsgleichung von HRID 719510
[N:1]1([CH2:7][C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(OC(Cl)=O)(C)C.C(N(CC)CC)C.[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44]3=[N:45][CH:46]=[N:47][C:48]([O:49][CH:50]4[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]4)=[C:43]3[CH:42]=[N:41]2)=[CH:36][CH:35]=1)(=[O:33])=[O:32]>CS(C)=O>[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44]3=[N:45][CH:46]=[N:47][C:48]([O:49][CH:50]4[CH2:55][CH2:54][N:53]([C:13]([C:11]5[O:12][C:8]([CH2:7][N:1]6[CH2:2][CH2:3][O:4][CH2:5][CH2:6]6)=[CH:9][CH:10]=5)=[O:15])[CH2:52][CH2:51]4)=[C:43]3[CH:42]=[N:41]2)=[CH:36][CH:35]=1)(=[O:32])=[O:33]

Komponenten

6

Edukt 4

HCID 7917Isopropyl chloroformateHCID 8471Triethylamine2×HCID 5805305-Morpholin-4-ylmethyl-furan-2-carboxylic acidHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 21897743{4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(5-morpholin-4-ylmethyl-furan-2-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

5-Morpholin-4-ylmethyl-furan-2-carboxylic acid (0.12 mmol, 25 mg), and isopropylchloroformate (0.12 mmol, 17 μL) and triethylamine (0.12 mmol, 17 μL) were dissolved in DMSO (2 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.12 mmol, 50 mg) and excess triethylamine were added. The mixture was heated in a microwave for 5 minutes at 120° C. The progress of the reaction was monitored by thin layer chromatography and LCMS. Purification by HPLC provided compound A116 as a white solid. LCMS (ESI), m/z 567.3 (MH+, 100%).

Aufarbeitung

  1. temperatureThe mixture was heated in a microwave for 5 minutes at 120° C
  2. customPurification by HPLC
  3. customprovided compound

Quellen und Nachweise

ORD-Eintrag
ord-1ee15c4976f54e6f820a9e9d6abab935
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132426B2

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