Lithium hydroxide, monohydrate → 1-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

HRID 1802178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802178
[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]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([O:27]CC)=[O:26])[CH:4]=[N:3]1.O.[OH-].[Li+]>CO.O>[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]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=[O:26])[CH:4]=[N:3]1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 67776104ethyl 1-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 677757071-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acidAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of ethyl 1-methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (1.22 g, 3.05 mmol) and lithium hydroxide monohydrate (641 mg, 15.3 mmol) in methanol (30 ml) and water (5 ml) is stirred for 6 hours at 50° C. The solvent is evaporated, the residue diluted with water, acidified to pH=0 with 2N aqueous hydrochloric acid. The precipitated solid is collected by filtration, washed with ethyl acetate and dried affording 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (851 mg, 75%) as a light yellow solid. MS: m/z=369.9 (M−H+).

Aufarbeitung

  1. customThe solvent is evaporated
  2. additionthe residue diluted with water
  3. filtrationThe precipitated solid is collected by filtration
  4. washwashed with ethyl acetate
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0a1e28de941342a2b7af5e3571aae3bb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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