Sodium Hydroxide → HCID 46213143, compound

HRID 1035798Notes

Reaction equation

HRID 1035798 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][CH:19]([N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH2:18][CH2:17]4)=[N:12][N:11]3[C:27]=2[C:28]2[CH:33]=[CH:32][N:31]=[C:30]3[N:34](S(C4C=CC(C)=CC=4)(=O)=O)[CH:35]=[CH:36][C:29]=23)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][CH:19]([N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH2:18][CH2:17]4)=[N:12][N:11]3[C:27]=2[C:28]2[CH:33]=[CH:32][N:31]=[C:30]3[NH:34][CH:35]=[CH:36][C:29]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58046361HCID 58046361, compound

Product 1

HCID 46213143HCID 46213143, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 2-(4-fluorophenyl)-6-(4-pyrrolidin-1-ylpiperidin-1-yl)-3-[1-(4-methylphenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine obtained in step 6.1 is dissolved in 3 ml of a mixture of methanol and tetrahydrofuran (2/1), then treated using 0.09 ml (0.54 mmol) of a 6N aqueous solution of sodium hydroxide at 60° C. for 1 and a half hours. The solvent is evaporated and the residue taken up in 3 ml of water. The product is extracted 2 times with 3 ml of dichloromethane. The organic phase is dried over sodium sulphate and the solvent is removed by evaporation under reduced pressure. The residue obtained is then purified by chromatography over a silica gel column (4 g) by eluting with a gradient of dichloromethane, methanol and aqueous ammonia (of 95/5/05 to 90/10/1) in order to give 0.064 g of 2-(4-fluorophenyl)-6-(4-pyrrolidin-1-ylpiperidin-1-yl)-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine after crystallization in 10 ml of acetonitrile, filtration and drying.

Workup

  1. additiontreated
  2. customat 60° C.
  3. customfor 1 and a half hours
  4. customThe solvent is evaporated
  5. extractionThe product is extracted 2 times with 3 ml of dichloromethane
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. customthe solvent is removed by evaporation under reduced pressure
  8. customThe residue obtained
  9. customis then purified by chromatography over a silica gel column (4 g)
  10. washby eluting with a gradient of dichloromethane, methanol and aqueous ammonia (of 95/5/05 to 90/10/1) in order

Sources & evidence

ORD record
ord-61683eb8237b468ca71ba7b9760f3dec
Source dataset
uspto-grants-2013_10
Patent number
US08546395B2

Reaction notes

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