7-Chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amine → Methyl 4-(7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoate

HRID 1256343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256343
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:15])[CH:3]=1.[Cl-].[CH3:17][O:18][C:19](=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:6]2[N:5]=[C:4]([NH:15][C:24]([C:23]2[CH:27]=[CH:28][C:20]([C:19]([O:18][CH3:17])=[O:29])=[CH:21][CH:22]=2)=[O:25])[CH:3]=1

Komponenten

5

Edukt 2

HCID 442513097-Chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amineHCID 53442854Terephthalic acid monomethylester chloride

Produkt 1

HCID 86652275Methyl 4-(7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)benzoateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amine (0.5 g, 1.0 equivalent) was suspended in pyridine (0.2 M) in a round bottom flask. At 0° C. was added a solution of terephthalic acid monomethylester chloride (2.0 equivalents) pre-dissolved in pyridine (0.8M), and followed by addition of N,N-dimethylpyridin-4-amine (0.1 equivalent). The mixture was stirred vigorously at 0° C. for 48 h. The reaction was quenched with saturated NaHCO3; pyridine was removed in vacuo and the residue was extracted with EtOAc twice and the combined organic layers were dried over Na2SO4. The organic layers were concentrated in vacuo and the crude mixture was purified using chromatography (SiO2, gradient of 10 to 50% EtOAc/hexanes) to afford the titled compound (10%) as a solid. Melting point (191.0-195.0° C.). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.90 (s, 3 H) 7.20 (s, 1 H) 8.06-8.11 (m, 2 H) 8.12-8.18 (m, 2 H) 8.32 (s, 1 H) 11.88 (s, 1 H); ESI-MS: m/z 399.0 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3
  2. custompyridine was removed in vacuo
  3. extractionthe residue was extracted with EtOAc twice
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationThe organic layers were concentrated in vacuo
  6. customthe crude mixture was purified

Quellen und Nachweise

ORD-Eintrag
ord-4de8a05115f44b76ac320e804d063ac9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461163B2

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