Diisopropylethylamine → ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1802249Notes

Reaction equation

HRID 1802249 reaction equation
[Br:1][C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](O)=[O:23])=[O:16])[CH3:13].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](=[O:23])[NH:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([Br:1])[N:11]=[C:5]2[CH:6]=1)=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677745572-Bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 67775496ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine (2.39 g, 11.2 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (2.22 g, 11.2 mmol), propylphosphonic anhydride (50% in ethyl acetate, 16.5 ml, 28.0 mmol) and N,N-diisopropylethylamine (5.72 ml, 33.7 mmol) in tetrahydrofuran (80 ml) was refluxed for 18 hours under argon atmosphere. The solvent was evaporated and the resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water 4 times and dried in vacuo affording 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.64 g, 82.5%) as a light yellow solid. mp: 177-180° C., MS: m/z=393.0/395.0 (M+H+)

Workup

  1. temperaturewas refluxed for 18 hours under argon atmosphere
  2. customThe solvent was evaporated
  3. customthe resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water 4 times
  6. customdried in vacuo

Sources & evidence

ORD record
ord-89a362b08e7e4e50b4380b5548f4dee0
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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