Hydrochloric Acid → 1-Benzyl-7-benzylamino-3-bromo-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734533Notes

Reaction equation

HRID 1734533 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13](Cl)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([Br:18])=[C:9]1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>C(N)C1C=CC=CC=1>[CH2:1]([N:8]1[C:12]2=[C:13]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([Br:18])=[C:9]1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 194377701-Benzyl-3-bromo-7-chloro-2-methylpyrrolo[2,3-d]pyridazine

Product 1

HCID 194377531-Benzyl-7-benzylamino-3-bromo-2-methylpyrrolo[2,3-d]pyridazine

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of 1.0 g (2.97 retool) of 1-benzyl-3 -bromo-7-chloro-2-methylpyrrolo [2,3-d]pyridazine in 5 ml of benzylamine is heated to 150° C. for 5 h and subsequently cooled to room temperature. The solution is then treated with 50 ml of water, adjusted to pH 6 with 2 N hydrochloric acid and extracted with 2×50 ml of dichloromethane. The organic extracts are dried over magnesium sulfate and concentrated. The residue which remains is chromatographed on silica gel (eluent: toluene/dioxane=2:1). After concentration of the fractions of Rf=0.25 and crystallization from diisopropyl ether, 1.01 g (84%) of the title compound are isolated. M.p.: 185°-188° C.

Workup

  1. extractionextracted with 2×50 ml of dichloromethane
  2. dry with materialThe organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue which remains is chromatographed on silica gel (eluent: toluene/dioxane=2:1)
  5. customAfter concentration of the fractions of Rf=0.25 and crystallization from diisopropyl ether, 1.01 g (84%) of the title compound
  6. customare isolated

Sources & evidence

ORD record
ord-2e5701863f444b899a50f5f4626ae5ea
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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