Propyl isocyanate → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-isopropylpiperidine-1-carboxamide

HRID 74879

Reaktionsgleichung

Reaktionsgleichung von HRID 74879
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[N:17]=[C:16]([NH:18][C@H]4CCCNC4)[C:15]([F:25])=[CH:14][N:13]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.ClC1C=C2C(C3N=C(N[C@H:43]4[CH2:48][CH2:47][CH2:46][NH:45][CH2:44]4)C(F)=CN=3)=CNC2=NC=1.[CH:50]([N:53]([CH:56](C)C)CC)([CH3:52])[CH3:51].N(CCC)=C=[O:61]>C(Cl)Cl.CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[N:17]=[C:16]([NH:18][CH:44]4[CH2:43][CH2:48][CH2:47][CH2:46][N:45]4[C:56]([NH:53][CH:50]([CH3:52])[CH3:51])=[O:61])[C:15]([F:25])=[CH:14][N:13]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 61033Propyl isocyanateHCID 81531DiisopropylethylamineHCID 67287751(S)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine hydrochlorideHCID 67287752(S)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine

Produkt 1

HCID 86762722(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-isopropylpiperidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine hydrochloride, 5b, (0.042 g, 0.100 mmol) in CH2Cl2 (1.4 mL) and DMF (0.3 mL) was added N,N-diisopropyl-N-ethylamine (0.300 mL, 1.720 mmol) followed by isocyanatopropane (0.120 mmol). The reaction mixture was stirred at room temperature for 17 hours. The mixture was concentrated in vacuo, dissolved in 1 mL of DMSO and purified by preparatory HPLC (0.1% ammonium formate-H2O/acetonitrile) to afford the desired product, 439.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in 1 mL of DMSO
  3. custompurified by preparatory HPLC (0.1% ammonium formate-H2O/acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-bf099035ea644ff28bab09c0ab868541
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829007B2

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