Methanol → 2-{4-[2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanol

HRID 1035794Notes

Reaction equation

HRID 1035794 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)=[N:12][N:11]3[C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[C:29]3[N:33](S(C4C=CC=CC=4)(=O)=O)[CH:34]=[CH:35][C:28]=23)=[CH:4][CH:3]=1.O1CCCC1.CO.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)=[N:12][N:11]3[C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[C:29]3[NH:33][CH:34]=[CH:35][C:28]=23)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58046369HCID 58046369, compound

Product 1

HCID 462130842-{4-[2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanolYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Added to a solution of 0.22 g (0.36 mmol) of 2-{4-[2-(4-fluorophenyl)-8-methyl-3-{1-[phenylsulphonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanol in 5 ml of a mixture of tetrahydrofuran and methanol (1/1), is 0.12 ml (0.72 mmol) of a 6N aqueous solution of sodium hydroxide. The mixture is heated at 50° C. for 1 hour, then poured into 20 ml of water. The product is extracted with dichloromethane. The organic phase is separated, dried over sodium sulphate and the solvent is removed by evaporation under reduced pressure. The yellowish residue obtained is then purified by chromatography on a silica gel column (40 g) by eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order to give 0.110 g of 2-{4-[2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanol after crystallization in 10 ml of acetonitrile, filtration and drying.

Workup

  1. extractionThe product is extracted with dichloromethane
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed by evaporation under reduced pressure
  5. customThe yellowish residue obtained
  6. customis then purified by chromatography on a silica gel column (40 g)
  7. washby eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order

Sources & evidence

ORD record
ord-5af5af7b21cb44d7afc1375f53e1a6c1
Source dataset
uspto-grants-2013_10
Patent number
US08546395B2

Reaction notes

Loading…