Diisopropylethylamine → ethyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate

HRID 1802177

Reaktionsgleichung

Reaktionsgleichung von HRID 1802177
[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.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](O)=[O:28])=[O:21])[CH3:18].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:30][N:25]1[C:26]([C:27](=[O:28])[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:22]([C:20]([O:19][CH2:17][CH3:18])=[O:21])[CH:23]=[N:24]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677741452-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine

Produkt 1

HCID 57377633ethyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylateAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (945 mg, 4.49 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (1.07 g, 5.39 mmol), propylphosphonic anhydride (50% in ethyl acetate, 6.62 ml, 11.2 mmol) and diisopropylethylamine (3.93 ml, 22.5 mmol) in tetrahydrofurane (50 ml) is stirred for 2.5 days at 25° C. The crude material is loaded on silicagel and purified by flash chromatography on a 50 g silica column using heptane/ethyl acetate 20-100% and then ethyl acetate/methanol 10-30% as eluent. The fractions containing product are evaporated to dryness and the residue (4.23 g light yellow solid) is dissolved in tetrahydrofurane (20 ml); sodium bicarbonate solution (30 ml) is added and the mixture is stirred for 30 minutes at 25° C. The solid is collected by filtration, washed with water and dried affording ethyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (1.336 g, 76.1%) as an off-white solid. mp.: 242-3° C. MS: m/z=391.2 (M+H+).

Aufarbeitung

  1. custompurified by flash chromatography on a 50 g silica column
  2. additionThe fractions containing product
  3. customare evaporated to dryness
  4. dissolutionthe residue (4.23 g light yellow solid) is dissolved in tetrahydrofurane (20 ml)
  5. additionsodium bicarbonate solution (30 ml) is added
  6. stirringthe mixture is stirred for 30 minutes at 25° C
  7. filtrationThe solid is collected by filtration
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-545cf32c63764463b661adc7171aa69d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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