Acetone → HCID 86696340, compound

HRID 870645Notes

Reaction equation

HRID 870645 reaction equation
[CH3:1][C:2]([CH3:4])=O.[Br:5][C:6]1[N:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1.[BH4-].[Na+]>CO>[Br:5][C:6]1[N:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][CH:2]([CH3:4])[CH3:1])[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 86696341HCID 86696341, compound

Product 1

HCID 86696340HCID 86696340, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetone [67-64-1] (2.0 mL, 43.5 mmol), then powdered, activated, 4 Angstrom molecular sieve were added to a solution of N1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine (367.2 mg, 1.4 mmol) in methanol (4.8 mL). The reaction vessel was closed and the mixture allowed to rapidly stir, at ambient temperature, for 17 h then its content rapidly transferred into a stirring suspension of sodium borohydride [16940-66-2] (0.3 g, 6.9 mmol) in methanol (50 mL). After 1 h the mixture was gravity filtered and the filtrate evaporated. The crude product was then taken up in ethyl acetate, washed with brine, dried (MgSO4) and evaporated to provide 196.9 mg of yellow solid. LRMS (ESI) m/z 312.0/314.0 [(M+H)]+, calc'd for C12H18BrN5: 312.21.

Workup

  1. customThe reaction vessel was closed
  2. waitAfter 1 h the mixture was
  3. filtrationgravity filtered
  4. customthe filtrate evaporated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-f382429918c041b3b866c33c6a54662b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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