2-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine → N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide

HRID 1256408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256408
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:9][CH:8]2[C:10](Cl)=[O:11])=[CH:3][CH:2]=1.[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH2:28])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1>N1C=CC=CC=1>[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH:28][C:10]([CH:8]3[CH2:9][CH:7]3[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:11])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1

Komponenten

4

Edukt 2

HCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amineHCID 767027172-(Pyridin-4-yl)cyclopropanecarbonyl chloride

Produkt 1

HCID 67064769N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In a round-bottomed flask was 2-(pyridin-4-yl)cyclopropanecarbonyl chloride (7D, 190 mg, 1.05 mmol) added in Pyridine (2 mL) to give a yellow suspension. 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 213 mg, 0.951 mmol) was added portionwise at 0° C. The temperature was slowly raised to room temperature. The reaction was quenched with saturated sodium bicarbonate and partitioned between ethyl acetate and water. The separated organic layer was dried over Mg2SO4, filtered, and concentrated under reduced pressure (3×100 mL). The reaction mixture was filtered and purified by preparatory, 5-95% (10 mM NH4HCO3 (aq)/10 mM NH4HCO3 in 20/80 (v/v) H2O/MeCN). Received 9 mg (3%) of yellow solid. 1H NMR (DMSO-d6) δ: 11.32 (s, 1H), 8.46 (d, J=6.1 Hz, 2H), 7.94-8.06 (m, 2H), 7.88 (s, 1H), 7.53-7.67 (m, 3H), 7.15-7.26 (m, 2H), 6.33 (s, 1H), 2.37 (s, 3H), 1.50-1.66 (m, 2H). ESI-MS: m/z 370.0 (M+H)+.

Aufarbeitung

  1. customIn a round-bottomed flask was
  2. customto give a yellow suspension
  3. customThe reaction was quenched with saturated sodium bicarbonate
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe separated organic layer was dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (3×100 mL)
  8. filtrationThe reaction mixture was filtered
  9. custompurified by preparatory, 5-95% (10 mM NH4HCO3 (aq)/10 mM NH4HCO3 in 20/80 (v/v) H2O/MeCN)

Quellen und Nachweise

ORD-Eintrag
ord-d8cc6483fd2e40f0b4729460b0cd380d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461163B2

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