Diisopropylethylamine → HCID 67775879, compound

HRID 1802232Notes

Reaction equation

HRID 1802232 reaction equation
[CH2:1]([N:3]([CH3:14])[C:4]1[N:13]=[C:7]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][N:6]2[N:5]=1)[CH3:2].[CH2:15]([O:17][C:18]([C:20]1[CH:21]=[N:22][N:23]([CH3:28])[C:24]=1[C:25](O)=[O:26])=[O:19])[CH3:16].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:15]([O:17][C:18]([C:20]1[CH:21]=[N:22][N:23]([CH3:28])[C:24]=1[C:25](=[O:26])[NH:12][C:9]1[CH:10]=[CH:11][N:6]2[N:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH3:14])[N:13]=[C:7]2[CH:8]=1)=[O:19])[CH3:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 67774144HCID 67774144, compound

Product 1

HCID 67775879HCID 67775879, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N2-ethyl-N2-methyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine (215 mg, 1.12 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (267 mg, 1.35 mmol), propylphosphonic anhydride (50% in ethyl acetate, 1.66 ml, 2.81 mmol) and N,N-diisopropylethylamine (574 μl, 3.37 mmol) in tetrahydrofuran (10 ml) was refluxed for 18 hours. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate 100% as eluent affording 5-[2-(ethyl-methyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (375 mg, 89.8%) as a light yellow solid. mp: 167° C., MS: m/z=372.5 (M+H+)

Workup

  1. temperaturewas refluxed for 18 hours
  2. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-512dde1ad3b640929b81c5bb042d30bd
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

Loading…