Diisopropylethylamine → 1-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1802239Notes

Reaction equation

HRID 1802239 reaction equation
[N:1]1([C:6]2[N:15]=[C:9]3[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][N:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](O)=[O:27])=[O:20])[CH3:17].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](=[O:27])[NH:14][C:11]1[CH:12]=[CH:13][N:8]2[N:7]=[C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[N:15]=[C:9]2[CH:10]=1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677741812-(Pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 677763851-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (197 mg, 969 μmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (231 mg, 1.16 mmol), propylphosphonic anhydride (50% in ethyl acetate, 1.43 ml, 2.42 mmol) and N,N-diisopropylethylamine (494 μl, 2.91 mmol) in tetrahydrofuran (10 ml) was refluxed for 18 hours. The solvent was evaporated, the residue was triturated with sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water and dried affording 1-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (327 mg, 88.0%) as a light brown solid. mp: 233-234° C., MS: m/z=384.5 (M+H+).

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue was triturated with sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7e3111d4b7dd4e74bf8d8c915318b1d3
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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