Sodium ethoxide → 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 724007

Reaktionsgleichung

Reaktionsgleichung von HRID 724007
CC[O-].[Na+].Cl.[CH:6]1([NH:11][C:12]([NH2:14])=[NH:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:24]([C:25](=O)[C:26]#[CH:27])=[C:18]2[CH:17]=1>C(O)C>[Cl:15][C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:24]([C:25]3[CH:26]=[CH:27][N:14]=[C:12]([NH:11][CH:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)[N:13]=3)=[C:18]2[CH:17]=1

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 221809211-[5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, Verbindung

Produkt 1

HCID 102238594-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium ethylate (0.7 mL (2.09 mmol), 210% in ethanol) and cyclopentyl guanidine hydrochloride (0.47 g, 2.88 mmol) were added sequentially to ethanol (30 mL). The resulting solution was stirred at room temperature for 30 minutes. 1-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-propyn-1-one (0.5 g, 1.61 mmol) was added, and the suspension was stirred at room temperature for 2 days. The reaction was quenched by the addition of water. The aqueous phase was extracted by ethyl acetate. The organics were combined, washed with brine and dried over magnesium sulfate. Filtration and concentration gave a solid. This solid was recrystallized from methanol to give 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.45 g, 66%) as a pale yellow solid. 1H NMR (CDCl3) δ 8.59 (b, 1H), 8.42 (d, 1H), 8.05 (d, 1H), 7.59 (d, 2H), 7.03 (d, 2H), 6.91 (dd, 1H), 6.39 (d, 1H), 5.34 (broad s, 1H), 4.42 (m, 1H), 3.92 (s, 3H), 2.17 (m, 2H), 1.86–1.60 (m, 6H); MS m/z 420 (M+1).

Aufarbeitung

  1. stirringthe suspension was stirred at room temperature for 2 days
  2. customThe reaction was quenched by the addition of water
  3. extractionThe aqueous phase was extracted by ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration
  7. customgave a solid
  8. customThis solid was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-a65ee26c3d8f484dbd82136678d4d9d7
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141569B2

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