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

HRID 1802198Notes

Reaction equation

HRID 1802198 reaction equation
[CH:1]([C:4]1[N:13]=[C:7]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:27])[C:23]=1[C:24](O)=[O:25])=[O:18])[CH3:15].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH:1]([C:4]1[N:13]=[C:7]2[CH:8]=[C:9]([NH:12][C:24]([C:23]3[N:22]([CH3:27])[N:21]=[CH:20][C:19]=3[C:17]([O:16][CH2:14][CH3:15])=[O:18])=[O:25])[CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677763492-Isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 67775033ethyl 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylateYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (159 mg, 902 μmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (215 mg, 1.08 mmol), propylphosphonic anhydride (50% in ethyl acetate, 1.33 ml, 2.26 mmol) and diisopropylethylamine (473 μl, 2.71 mmol) in tetrahydrofurane (7 ml) is refluxed for 18 hours. The solvent is evaporated and the residue stirred for 1 hr with sat. aqueous sodium hydrogencarbonate solution. The precipitated solid is collected by filtration, washed with water and dried affording ethyl 5-(2-isopropyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (332 mg, 103%) as a white solid. Mp.: 175-7° C. MS: m/z=357.2 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated
  3. filtrationThe precipitated solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7ccb1ee00c214cdebb0c8606c743b66d
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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