Ethylamine hydrochloride → 7-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethylamide

HRID 1802245Notes

Reaction equation

HRID 1802245 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:27])[C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[C:22]([C:24]([OH:26])=O)[N:23]=[C:17]3[CH:16]=2)=[O:13])=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl.[CH2:29]([NH2:31])[CH3:30]>>[CH2:29]([NH:31][C:24]([C:22]1[N:23]=[C:17]2[CH:16]=[C:15]([NH:14][C:12]([C:11]3[N:10]([CH3:27])[N:9]=[CH:8][C:7]=3[C:5]([N:1]3[CH2:4][CH2:3][CH2:2]3)=[O:6])=[O:13])[CH:20]=[CH:19][N:18]2[N:21]=1)=[O:26])[CH3:30]

Participants

3

Reactant 2

HCID 11198Ethylamine hydrochlorideHCID 677751337-(4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxamido)-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid

Product 1

HCID 573782907-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethylamideYield 36.3%

Procedure

The product was prepared in the same manner as described in example 62 using 7-(4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxamido)-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid (130 mg, 264 μmol) and ethanamine hydrochloride (215 mg, 2.64 mmol) as starting materials. The reactions affords 7-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethylamide (38 mg, 36.3%) as a white solid. mp: 217-229° C., MS: m/z=397.1 (M+H+)

Workup

  1. customThe product was prepared in the same manner

Sources & evidence

ORD record
ord-389e6b8e4bd8463bafcad7321b051dd7
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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