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Sodium ethoxide → 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 1269069
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1269069
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[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:24]([C:25](=O)[C:26]#[CH:27])=[C:20]2[CH:19]=[CH:18][CH:17]=1>C(O)C>[Cl:15][C:16]1[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[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:20]2[CH:19]=[CH:18][CH:17]=1
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Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 184465971-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, Verbindung

Produkt 1

HCID 111768674-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Sodium ethylate solution (21% T, 0.5 mL, 1.43 mmol) was added to ethanol followed by cyclopentylguanidine hydrochloride (323 mg, 1.98 mmol). The mixture was stirred at room temperature for 30 minutes. 1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (313 mg, 1.10 mmol) was added to the resultant solution and stirred at room temperature for 15 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue. The phases were separated, the organic phase dried (magnesium sulfate), filtered and concentrated. The residue was recrystallized from ethyl acetate. 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (280 mg, 65%) was obtained as a yellow solid. 1H-NMR (CDCl3): δ 8.50 (d, 1H), 8.15 (d, 1H), 7.49 (d, 1H), 7.27 (t, 1H), 7.06 (d, 1H), 6.41 (d, 1H), 6.36 (d, 1H), 5.10 (d, 1H), 4.35 (m, 1H), 2.12 (s, 3H), 2.08 (m, 2H), 1.78–1.53 (m, 6H). MS m/z 394 (M+1).

Aufarbeitung

  1. stirringstirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionEthyl acetate and water were added to the residue
  4. customThe phases were separated
  5. dry with materialthe organic phase dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2dca8a713af54b93ae23f86125a1076a
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199120B2

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