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

HRID 1802193Notes

Reaction equation

HRID 1802193 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:4]2[CH:3]=1.[N:16]1([C:20]([C:22]2[CH:23]=[N:24][N:25]([CH3:30])[C:26]=2[C:27](O)=[O:28])=[O:21])[CH2:19][CH2:18][CH2:17]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:14]([O:13][C:11]([C:9]1[N:10]=[C:4]2[CH:3]=[C:2]([NH:1][C:27]([C:26]3[N:25]([CH3:30])[N:24]=[CH:23][C:22]=3[C:20]([N:16]3[CH2:19][CH2:18][CH2:17]3)=[O:21])=[O:28])[CH:7]=[CH:6][N:5]2[N:8]=1)=[O:12])[CH3:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 58446922HCID 58446922, compoundHCID 67776028Ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

Product 1

HCID 677752457-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethyl esterYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (540 mg, 2.62 mmol), 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (548 mg, 2.62 mmol), propylphosphonic anhydride (50% in ethyl acetate, 3.86 ml, 6.55 mmol) and diisopropylethylamine (1.37 ml, 7.86 mmol) in tetrahydrofurane (10 ml) is refluxed for 18 hours. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The precipitated solid is collected by filtration, washed several times with water and dried affording 7-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (665 mg, 63.9%) as a light brown solid. mp.: 252-5° C. MS: m/z=398.2 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated
  3. customthe residue triturated with sat. aqueous sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid is collected by filtration
  5. washwashed several times with water
  6. customdried

Sources & evidence

ORD record
ord-75502040c1d3433d8c7c67fb2ddc3f38
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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