(R)-3-Pyrrolidinol → (3R)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-3-ol

HRID 925607Notes

Reaction equation

HRID 925607 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16](Cl)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.[NH:20]1[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]1>C(O)CCC>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([N:20]3[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]3)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 71491928HCID 71491928, compound

Product 1

HCID 71145051(3R)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

150 mg (0.56 mmol) 3-(1-benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine and 206.2 mg (1.67 mmol) (3R)-pyrrolidin-3-ol in 5.0 mL butan-1-ol were stirred 72 h at 150° C. The solvent was removed. The residue was purified by HPLC to yield 23 mg (13%).

Workup

  1. customThe solvent was removed
  2. customThe residue was purified by HPLC
  3. customto yield 23 mg (13%)

Sources & evidence

ORD record
ord-95422946872e478b86496e944c9c4e70
Source dataset
uspto-grants-2016_03
Patent number
US09284319B2

Reaction notes

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