Ethyl Acetate → ethyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylate

HRID 1844433Notes

Reaction equation

HRID 1844433 reaction equation
[C:1]1([C:7]2[N:16]=[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](O)=[O:28])=[O:21])[CH3:18].CCCP(=O)=O.C(OCC)(=O)C.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](=[O:28])[NH:15][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:16]=2)[CH:14]=1)=[O:21])[CH3:18]

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6108092-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-amineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 89464100ethyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-ylamine (300 mg, 1.43 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (339 mg, 1.71 mmol), propylphosphonic anhydride in ethyl acetate 50% (2.27 g, 2.1 ml, 3.57 mmol) and diisopropylethyl amine (553 mg, 748 μl, 4.28 mmol) in tetrahydrofuran (10 ml) was refluxed for 2.5 days. The mixture was evaporated and the residue was treated with saturated aqueous sodiumhydrogen carbonate and stirred for 30 minutes. The solid was filtered off, washed with water and dried, affording 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (483 mg, 87%) as brown solid. Mp.: 251-254° C. MS: m/z=391.1 (M+H+).

Workup

  1. temperaturewas refluxed for 2.5 days
  2. customThe mixture was evaporated
  3. additionthe residue was treated with saturated aqueous sodiumhydrogen carbonate
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-1cdbeeecc2934386bad74714e3d33faa
Source dataset
uspto-grants-2015_02
Patent number
US08946427B2

Reaction notes

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