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Hydrochloric Acid → 4-Bromo-N-(5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide

HRID 2120764
Notes
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Reaction equation

HRID 2120764 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([NH2:12])[N:11]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.C[Al](C)C.C[O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=1)=O.Cl>O1CCOCC1.C1(C)C=CC=CC=1>[Br:33][C:30]1[CH:31]=[CH:32][C:27]([C:25]([NH:12][C:10]2[N:11]=[C:7]3[C:6]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]3[N:9]=2)=[O:24])=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12081Methyl 4-bromobenzoateHCID 16682925TrimethylaluminumHCID 234358815-Methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine

Product 1

HCID 102738284-Bromo-N-(5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamideYield 15%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 24 mg (0.1 mmol) 5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine in 1 ml dioxane was added 0.4 ml (0.4 mmol) of a 1 M solution of AlMe3 in toluene and allowed to stir for 1 h at room temperature. 86 mg (0.4 mmol) 4-bromo-phenyl carboxylic acid methyl ester in I ml dioxane was added and the mixture was stirred for 48 h at 90° C. 0.5 ml 1N HCl aq. was added and the mixture was evaporated to dryness. The residue was taken up in 1.5 ml formic acid and 0.5 ml methanol and subjected to reversed phase HPLC chromatography eluting with a water/acetonitrile gradient. Evaporation of the eluents yielded 6 mg (15%) of the title compound. MS m/e (%): 423.3 (M+H+, 100).

Workup

  1. stirringthe mixture was stirred for 48 h at 90° C
  2. customthe mixture was evaporated to dryness
  3. washeluting with a water/acetonitrile gradient
  4. customEvaporation of the eluents

Sources & evidence

ORD record
ord-ff8bd5bf6abf4716a704c2e934c7851d
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06693116B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes