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Pyridine → N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide

HRID 1256422
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1256422
Br[C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:12]3[N:21]=[CH:22][CH:23]=[C:11]3[N:10]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=C[CH:27]=1.[F:32][C:33]([F:45])([F:44])[O:34]C1C=CC(C(Cl)=O)=CC=1>>[CH3:27][C:22]1[CH:23]=[C:11]2[N:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:24]=[CH:25][C:2]([O:34][C:33]([F:45])([F:44])[F:32])=[CH:3][CH:4]=3)[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:12]2[N:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 670644084-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide

Produkt 1

HCID 67064576N-(2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamideAusbeute 69,2 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 2-methyl-7-morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9B, 52 mg, 0.151 mmol) and pyridine (60 mg, 0.467 mmol) was cooled to 0° C. and treated with 4-trifluoromethoxybenzoyl chloride (78 mg, 0.395 mmol). After stirring for 30 min, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate (5 mL). The aqueous mixture was extracted with ethyl acetate and the combined organics dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was dissolved in DMF/DMSO, filtered, and purified via preparative HPLC (60-80% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow solid (44.0 mg, 41%). Melting point (226.2-226.3° C.). 1H NMR (DMSO-d6) δ: 11.10 (s, 1H), 8.01-8.27 (m, 2H), 7.51 (dd, J=9.0, 0.9 Hz, 2H), 7.30 (s, 1H), 6.18 (s, 1H), 3.79-3.91 (m, 4H), 3.69-3.75 (m, 4H), 2.38 (s, 3H); ESI-MS: m/z 422.1 (M+H)+. Melting point (226.2-226.3° C.).

Aufarbeitung

  1. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate (5 mL)
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. dry with materialthe combined organics dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was dissolved in DMF/DMSO
  7. filtrationfiltered
  8. custompurified via preparative HPLC (60-80% MeCN/H2O gradient+0.01% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-fda7b905a65647b297474917a1256744
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461163B2

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