p-Toluenesulfonic acid monohydrate → 5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine

HRID 1842687

Reaktionsgleichung

Reaktionsgleichung von HRID 1842687
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[C:5]([Cl:17])=[CH:4][N:3]=1.[F:18][C:19]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][C:22]([NH2:23])=[C:21]([O:29][CH3:30])[CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)CCC>[Cl:17][C:5]1[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:7][C:2]([NH:23][C:22]2[CH:24]=[C:25]([N+:26]([O-:28])=[O:27])[C:19]([F:18])=[CH:20][C:21]=2[O:29][CH3:30])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 574290724-Fluoro-2-methoxy-5-nitroaniline2×HCID 59291162HCID 59291162, Verbindung2×

Produkt 1

HCID 712393485-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 223862-PentanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(2,5-dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (Intermediate 21, 1.4 g, 5.28 mmol), 4-fluoro-2-methoxy-5-nitroaniline (Intermediate 23, 1.032 g, 5.55 mmol) and p-toluenesulfonic acid monohydrate (1.105 g, 5.81 mmol) was heated at 125° C. in 2-pentanol (40 mL) for 18 h. The mixture was then cooled and a solid was collected by filtration. The solid was washed with CH3OH and diethyl ether, and was then dried on the filter to give the title compound (1.73 g, 79%) as a yellow powder; 1H NMR: 3.98 (3H, s), 7.16 (1H, td), 7.33-7.48 (2H, m), 8.49 (1H, d), 8.53 (1H, d), 8.66 (1H, d), 8.86 (1H, d), 8.90 (1H, s), 8.96 (1H, s).

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. filtrationa solid was collected by filtration
  3. washThe solid was washed with CH3OH and diethyl ether
  4. customwas then dried on the
  5. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-3fc0b6858c184b5bb8ec48eb21365d88
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946235B2

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