Hydrazine hydrate (1:1) → 3-((2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 455135Notes

Reaction equation

HRID 455135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:22]=[C:21]([C:23]([O:25]CC)=O)[O:20][N:19]=2)=[CH:4][CH:3]=1.[NH2:28][NH2:29].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:22]=[C:21]([C:23]([NH:28][NH2:29])=[O:25])[O:20][N:19]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67028744HCID 67028744, compound

Product 1

HCID 670286833-((2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carbohydrazideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate (10.5 mmol, 4.0 g) in MeOH (50 mL) was cooled to 0° C., and 99% NH2NH2.H2O (62.8 mmol, 3.2 g) was then added dropwise. In the period of addition, lots of white precipitate was generated, kept stirring for 15 mins, the white solid was collected by filtration. The white solid was dispersed into MeOH again, sonicated for 10 mins, filtered, to give the final product (3.3 g, 86.0%). m/e+=369 (M+H+). 1H NMR (400 MHz, in DMSO-d6): δ 10.9-10.5 (1H, D, brd, NH), δ 8.44-8.42 (1H, D, d, J=6.8 Hz, ArH), δ 7.87-7.85 (2H, D, dd, J=6.4, 1.6 Hz, ArH), δ 7.67-7.64 (1H, D, d, J=9.2 Hz, ArH), δ 7.56-7.54 (2H, D, dd, J=6.4, 1.6 Hz, ArH), δ 7.38-7.25 (1H, D, m, ArH), δ 5.01-4.75 (2H, D, brd, NH2), δ 4.75 (2H, D, s, CH2).

Workup

  1. additionIn the period of addition, lots of white precipitate
  2. filtrationthe white solid was collected by filtration
  3. additionThe white solid was dispersed into MeOH again
  4. customsonicated for 10 mins
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cde0f97ea2ef4c39b9ded6308c240bbd
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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