N-bromobutanimide → (3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

HRID 718712Notes

Reaction equation

HRID 718712 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1>CC#N>[Br:25][C:13]1[N:9]2[N:10]=[CH:11][CH:12]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:8]2=[N:15][C:14]=1[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 117728752(8-Morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Product 1

HCID 117728706(3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of compound 5d (40.0 g, 171 mmol) in CH3CN (400 mL) was treated dropwise with a solution of NBS (30.2 g, 170 mmol) in CH3CN (906 mL) at −20° C. After addition, the reaction mixture was stirred for 2 h at room temperature. The reaction was quenched by the addition of 50 mL of saturated Na2S2O3 solution. The solids formed were collected by filtration and washed with diethyl ether to afford compound 83a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C11H13BrN4O2: 313.0 (M+H). found: 313.0.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched by the addition of 50 mL of saturated Na2S2O3 solution
  3. customThe solids formed
  4. filtrationwere collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-cff34138d71540a6ac2d3c1c8da7bb51
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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