Diisopropylethylamine → HCID 57378953, Verbindung

HRID 1802140

Reaktionsgleichung

Reaktionsgleichung von HRID 1802140
[C:1]1([C:7]2[N:16]=[C:10]3[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](O)=[O:27])=[O:20].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:29][N:24]1[C:25]([C:26](=[O:27])[NH:15][C:12]2[CH:13]=[CH:14][N:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:16]=[C:10]3[CH:11]=2)=[C:21]([C:19]([O:18][CH3:17])=[O:20])[CH:22]=[N:23]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 459236814-(Methoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677741452-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine

Produkt 1

HCID 57378953HCID 57378953, VerbindungAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (1.534 g, 7.3 mmol), 4-(methoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (1.61 g, 8.76 mmol), propylphosphonic anhydride (50% in ethyl acetate, 10.7 ml, 18.2 mmol) and diisopropylethylamine (5.1 ml, 29.2 mmol) in tetrahydrofurane (54 ml) is stirred at 70° C. for 1.25 hr giving a white suspension. The cooled suspension is poured in sat. aqueous sodium bicarbonate solution (200 ml), stirred at room temperature for 15 min and the solid is collected by filtration, washed with water and dried affording methyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (2.596 g, 94.5%) as a white solid. mp.: 243-7° C. MS: m/z=377.2 (M+H+).

Aufarbeitung

  1. customgiving a white suspension
  2. filtrationthe solid is collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-855055d4ec904c1a96d094e383d2d916
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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