Diisopropylethylamine → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide

HRID 1802187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802187
[F:1][C:2]1[C:3]([NH2:17])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[N:18]1([C:22]([C:24]2[CH:25]=[N:26][N:27]([CH3:32])[C:28]=2[C:29](O)=[O:30])=[O:23])[CH2:21][CH2:20][CH2:19]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[F:1][C:2]1[C:3]([NH:17][C:29]([C:28]2[N:27]([CH3:32])[N:26]=[CH:25][C:24]=2[C:22]([N:18]2[CH2:21][CH2:20][CH2:19]2)=[O:23])=[O:30])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 58446922HCID 58446922, VerbindungHCID 677751876-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Produkt 1

HCID 573777414-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amideAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (50 mg, 219 μmol), 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (45.8 mg, 219 μmol), propylphosphonic anhydride (50% in ethyl acetate, 323 μl, 548 μmol) and diisopropylethyl amine (115 μl, 657 μmol) in tetrahydrofuran (5 ml) was refluxed for 18 hours. The crude material is loaded on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 20-100% as eluent, affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (40 mg: 43.5%) as white solid. Mp.: >250° C. MS: m/z=420.3 (M+H+).

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. custompurified by flash chromatography on a 20 g silica column

Quellen und Nachweise

ORD-Eintrag
ord-ba28fd6c46754f0494c5c8f23b8acb9a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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