Sodium Bicarbonate → {(3S)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-3-yl}methanol

HRID 925608Notes

Reaction equation

HRID 925608 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.Cl.[NH:21]1[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22]1.C(=O)([O-])O.[Na+]>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:21]3[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22]3)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 43810917(3S)-pyrrolidin-3-ylmethanol hydrochlorideHCID 71491928HCID 71491928, compound

Product 1

HCID 71144923{(3S)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

150 mg (0.56 mmol) 3-(1-benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine, 183.7 mg (1.34 mmol) (3S)-pyrrolidin-3-ylmethanol hydrochloride (1:1) and 186.9 mg (2.23 mmol) sodium hydrogencarbonate in 4.0 mL butan-1-ol were stirred 72 h at 150° C. The solvent was removed. The residue was purified by HPLC to yield 65 mg (35%).

Workup

  1. customThe solvent was removed
  2. customThe residue was purified by HPLC
  3. customto yield 65 mg (35%)

Sources & evidence

ORD record
ord-19399e5690ec4cdea8bd8b3f7768d96c
Source dataset
uspto-grants-2016_03
Patent number
US09284319B2

Reaction notes

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