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

HRID 588435

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-fd719b818440472aad255ea0188e3d03
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227970B2

Linked notes

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