3-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine → N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-2-(cyclopentyloxy)acetamide

HRID 1912939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912939
[CH:1]1([O:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH2:29])=[N:20][N:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)=[CH:14][C:13]=1[CH3:30]>N1C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH:29][C:8](=[O:9])[CH2:7][O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:20][N:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)=[CH:14][C:13]=1[CH3:30]

Komponenten

4

Edukt 2

HCID 687470433-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amineHCID 866419172-(Cyclopentyloxy)acetyl chloride

Produkt 1

HCID 68749628N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-2-(cyclopentyloxy)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

The product from Example 133C (1.0 mL of solution in CH2Cl2) was added to a stirring solution of the product from Example 47C (51 mg, 0.178 mmol) in pyridine (1.4 mL). The reaction mixture was stirred at room temperature for 2 hours, and then quenched by addition of MeOH (0.5 mL). After 30 min, concentrated NH4OH (0.2 mL) was added, and the mixture was stirred at room temperature for 12 hours, and then concentrated under vacuum. The residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100) to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 1.52-1.81 (m, 8H) 2.42 (s, 3H) 2.56 (s, 3H) 2.73 (d, J=1.0 Hz, 3H) 4.05-4.12 (m, 1H) 4.09 (s, 2H) 6.86-6.89 (q, J=1.0 Hz, 1H) 7.40 (d, J=8.5 Hz, 1H) 7.54 (dd, J=8.4, 1.9 Hz, 1H) 7.65 (d, J=1.9 Hz, 1H); MS (DCI/NH3) m/z 413/415 (M+H)+.

Aufarbeitung

  1. customquenched by addition of MeOH (0.5 mL)
  2. waitAfter 30 min
  3. additionconcentrated NH4OH (0.2 mL) was added
  4. stirringthe mixture was stirred at room temperature for 12 hours
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100)

Quellen und Nachweise

ORD-Eintrag
ord-9d01b86a77284d3ca2323975d881efb7
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609669B2

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