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

HRID 1802240Notes

Reaction equation

HRID 1802240 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:24]([O:26]CC)=[O:25])[CH:4]=[N:3]1.O.[OH-].[Li+]>CO.O>[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([N:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:24]([OH:26])=[O:25])[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 677763851-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 677751361-methyl-5-(2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acidYield 106%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 1-methyl-5-(2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (322 mg, 840 μmol) and lithium hydroxide hydrate (141 mg, 3.36 mmol) in methanol (20 ml) and water (5 ml) was stirred for 2.5 days at 25° C. The solvent was evaporated, the residue was acidified with hydrochloric acid 37% to pH=0, the precipitated solid was filtered off, washed with water and dried affording 1-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (316 mg, 106%) as an off-white solid. mp: >250° C., MS: m/z=356.4 (M+H+)

Workup

  1. customThe solvent was evaporated
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6e9a1f01e05e4493a58a46d60911cb40
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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