N-Methylethylamine → N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide

HRID 1802143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802143
[CH3:1][N:2]1[C:6]([C:7](=[O:24])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=O)[CH:4]=[N:3]1.[CH2:28]([NH:30][CH3:31])[CH3:29].CCCP(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH2:28]([N:30]([CH3:31])[C:25]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:17]=[C:11]2[CH:10]=1)=[O:24])=[O:27])[CH3:29]

Komponenten

6

Edukt 3

HCID 12219N-MethylethylamineHCID 16167369Propylphosphoric anhydrideHCID 573789541-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 57378956N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamideAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (600 mg, 1.66 mmol), N-ethylmethylamine (427 ul, 4.97 mmole), N-diisopropylethylamine (868 ul, 4.97 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 2.44 ml, 4.14 mmol) in tetrahydrofurane (30 ml) is stirred for 2 hours at 70° C. The cooled solution is diluted with ethyl acetate, washed once with sat. aqueous sodium bicarbonate solution, once with brine, dried with magnesium sulfate and evaporated to dryness. Two successive crystallizations of the residue (680 mg white solid) from ethyl acetate afford N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (365 mg, 54.6%) as a white solid. mp.: 193-4° C. MS: m/z=404.3 (M+H+).

Aufarbeitung

  1. washwashed once with sat. aqueous sodium bicarbonate solution, once with brine
  2. dry with materialdried with magnesium sulfate
  3. customevaporated to dryness
  4. customTwo successive crystallizations of the residue (680 mg white solid) from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a5639e7330b74f1ca8e0ff136af6af50
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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