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1H-1,2,4-Triazole → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1H-1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79435
Notes
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Reaction equation

HRID 79435 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[CH2:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[NH:19][C:20]([C:22]2[N:26]3[CH:27]=[CH:28][C:29](F)=[CH:30][C:25]3=[N:24][CH:23]=2)=[O:21])[N:12]([CH2:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][CH3:39])[N:34]=2)[N:11]=1)[CH3:9]>C1OCCOC1.CN(C)C=O>[CH2:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[NH:19][C:20]([C:22]2[N:26]3[CH:27]=[CH:28][C:29]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)=[CH:30][C:25]3=[N:24][CH:23]=2)=[O:21])[N:12]([CH2:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][CH3:39])[N:34]=2)[N:11]=1)[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 67259540N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67259791N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1H-1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

1H-1,2,4-triazole was dissolved in 4-dioxane and treated with sodium hydride (20 mg, 0.48 mmol, 60% dispersion in mineral oil) with stirring at ambient temperature for 30 minutes. N-(3-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (35 mg, 0.08 mmol) was added as a solution in N,N-dimethylformamide. The mixture was heated to 98° C. and stirred for 2 days. The mixture was quenched by the addition of water. A precipitate formed and the solid was isolated by filtration, washed with water and dried under vacuum to give N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(1H-1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide as a white solid (39 mg). MS m/z 481.1 (M+1, APCI+).

Workup

  1. temperatureThe mixture was heated to 98° C.
  2. stirringstirred for 2 days
  3. customThe mixture was quenched by the addition of water
  4. customA precipitate formed
  5. customthe solid was isolated by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-1f8068529cd949d78e37560e39bb2b71
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes