2-Methylpyridine-4-boronic acid → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(2-methyl-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide

HRID 1802253Notes

Reaction equation

HRID 1802253 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:25])[C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[C:22](Br)[N:23]=[C:17]3[CH:16]=2)=[O:13])=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:26][C:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29][N:28]=1>>[CH3:26][C:27]1[CH:32]=[C:31]([C:22]2[N:23]=[C:17]3[CH:16]=[C:15]([NH:14][C:12]([C:11]4[N:10]([CH3:25])[N:9]=[CH:8][C:7]=4[C:5]([N:1]4[CH2:4][CH2:3][CH2:2]4)=[O:6])=[O:13])[CH:20]=[CH:19][N:18]3[N:21]=2)[CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 573782924-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 573783884-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(2-methyl-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amideYield 22%

Procedure

The product was prepared in the same manner as described in example 66 using 4-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide (150 mg, 371 μmol) and 2-methylpyridin-4-ylboronic acid (76.2 mg, 557 μmol) as starting materials. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 10% as eluent affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(2-methyl-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (34 mg, 22.0%) as an off-white solid. mp: 210-211° C., MS: m/z=417.4 (M+H+)

Workup

  1. customThe product was prepared in the same manner
  2. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-4ebaa84d624744cba1df23c398f45e6c
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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