Ethyl Acetate → 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 588434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588434
[N:1]1([C:7]2[N:16]=[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][N:9]3[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]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(OCC)(=O)C.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](=[O:28])[NH:15][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([N:8]=[C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=2)[CH:14]=1)=[O:21])[CH3:18]

Komponenten

7

Edukt 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 894644042-Morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-amine

Produkt 1

HCID 894647211-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-amine (225 mg, 1.03 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (224 mg, 1.13 mmol), propylphosphonic anhydride in ethyl acetate 50% (1.63 g, 1.51 ml, 2.57 mmol) and N,N-diisopropylethylamine (398 mg, 524 μl, 3.08 mmol) in tetrahydrofuran (7 ml) was refluxed for 18 hours. The solvent was evaporated, the residue was triturated with saturated aqueous sodium hydrogen carbonate. The precipitated solid was filtered off, washed with water and dried in vacuo, affording 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (292 mg, 71%) as light brown solid. Mp.: 233.5° C. MS: m/z=400.1 (M+H+).

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue was triturated with saturated aqueous sodium hydrogen carbonate
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ad18e2ec1fe3413db8e1137c04b9f4da
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227970B2

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