Hydrazine hydrate (1:1) → HCID 10790603, compound

HRID 1290189Notes

Reaction equation

HRID 1290189 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:35])[C:21](=[O:34])[CH2:22][N:23]4C(=O)C5=CC=CC=C5C4=O)[C:14]=3[Cl:36])[C:5]2=[N:4][C:3]=1[CH3:37].O.NN>CO>[NH2:23][CH2:22][C:21]([N:20]([C:15]1[C:14]([Cl:36])=[C:13]([C:18]([Cl:19])=[CH:17][CH:16]=1)[CH2:12][O:11][C:10]1[C:5]2[N:6]([C:2]([Br:1])=[C:3]([CH3:37])[N:4]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:35])=[O:34]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 10603670HCID 10603670, compound

Product 1

HCID 10790603HCID 10790603, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-bromo-8-[2,6-dichloro-3-(N-methyl-N-phthalimidoacetylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (450 mg) and hydrazine hydrate (41 mg) in methanol (5 ml) were refluxed for 30 minutes, and hydrazine hydrate (41 mg) was added thereto, and further, the mixture was refluxed for 1.5 hours. The resulting precipitates were filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in chloroform and the solution was washed with water twice and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized with diethyl ether to give 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-3-bromo-2-methylimidazo[1,2-a]pyridine (338 mg).

Workup

  1. temperaturewere refluxed for 30 minutes
  2. temperaturefurther, the mixture was refluxed for 1.5 hours
  3. customThe resulting precipitates
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe residue was dissolved in chloroform
  7. washthe solution was washed with water twice
  8. dry with materialbrine, dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized with diethyl ether

Sources & evidence

ORD record
ord-99323d1f36a14dffabf0e3239ce0ace2
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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