Lithium hydroxide, monohydrate → 1-Methyl-5-(2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

HRID 1844453Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:29])[C:10]=1[C:11](=[O:28])[NH:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([N:19]=[C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:21]=2)[CH:18]=1)=[O:5])C.O.[OH-].[Li+]>CO.O>[CH3:29][N:9]1[C:10]([C:11](=[O:28])[NH:12][C:13]2[CH:14]=[CH:15][C:16]3[N:17]([N:19]=[C:20]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[N:21]=3)[CH:18]=2)=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (282 mg, 0.71 mmol) and lithium hydroxide hydrate (88.9 mg, 2.12 mmol) in methanol (10 ml) and water (3 ml) was stirred for 18 hours at 55° C. The solvents were evaporated under reduced pressure and the residue treated with water (5 ml) and hydrogen chloride (1 molar in water, 2.12 ml). The precipitated solid was filtered off, washed with water and dried under reduced pressure, affording 1-methyl-5-(2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (187 mg, 71%) as light brown solid. Mp.: 294° C. MS: m/z=372.0 (M+H+).

Workup

customThe solvents were evaporated under reduced pressure
additionthe residue treated with water (5 ml) and hydrogen chloride (1 molar in water, 2.12 ml)
filtrationThe precipitated solid was filtered off
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-30e709e22de147009e98889746df443f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946427B2

Reaction notes

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