Diisopropylethylamine → 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1802263Notes

Reaction equation

HRID 1802263 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:12]([OH:14])=O)=[O:5])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([C:47]2[N:56]=[C:50]3[CH:51]=[C:52]([NH2:55])[CH:53]=[CH:54][N:49]3[N:48]=2)[CH:44]=[CH:45][CH:46]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:12](=[O:14])[NH:55][C:52]1[CH:53]=[CH:54][N:49]2[N:48]=[C:47]([C:43]3[CH:44]=[CH:45][CH:46]=[C:41]([O:40][CH3:39])[CH:42]=3)[N:56]=[C:50]2[CH:51]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677739812-(3-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 677766035-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-methyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester (8.0 g, 40.4 mmol) in DMF (120 ml) were added HATU (34 g, 88.9 mmol), 2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (10.6 g, 44.4 mmol) and DIPEA (30 ml, 161.1 mmol) at 0° C. The reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with water. The resultant precipitated solid was filtered, washed with water, dried azeotropically with toluene followed by vacuum to yield 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester as white solid (7.8 g, 56%). LC-MS: m/z=421.2 [M+H]+.

Workup

  1. customThe resultant precipitated solid
  2. filtrationwas filtered
  3. washwashed with water
  4. dry with materialdried azeotropically with toluene

Sources & evidence

ORD record
ord-64178b1d0fcc4844b497f065f3e0c146
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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