Diisopropylethylamine → HCID 57378953, compound

HRID 1802140

Reaction equation

HRID 1802140 reaction equation
[C:1]1([C:7]2[N:16]=[C:10]3[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][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].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:29][N:24]1[C:25]([C:26](=[O:27])[NH:15][C:12]2[CH:13]=[CH:14][N:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:16]=[C:10]3[CH:11]=2)=[C:21]([C:19]([O:18][CH3:17])=[O:20])[CH:22]=[N:23]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 459236814-(Methoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677741452-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine

Product 1

HCID 57378953HCID 57378953, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (1.534 g, 7.3 mmol), 4-(methoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (1.61 g, 8.76 mmol), propylphosphonic anhydride (50% in ethyl acetate, 10.7 ml, 18.2 mmol) and diisopropylethylamine (5.1 ml, 29.2 mmol) in tetrahydrofurane (54 ml) is stirred at 70° C. for 1.25 hr giving a white suspension. The cooled suspension is poured in sat. aqueous sodium bicarbonate solution (200 ml), stirred at room temperature for 15 min and the solid is collected by filtration, washed with water and dried affording methyl 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylate (2.596 g, 94.5%) as a white solid. mp.: 243-7° C. MS: m/z=377.2 (M+H+).

Workup

  1. customgiving a white suspension
  2. filtrationthe solid is collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-855055d4ec904c1a96d094e383d2d916
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Linked notes

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