Water → HCID 46213083, compound

HRID 1035792Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

Added to a solution of 0.230 g (0.40 mmol) of 2-(4-fluorophenyl)-6-[(3R)-3-methylpiperazin-1-yl]-3-{1-[(4-methylphenyl)sulphonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}imidazo[1,2-b]pyridazine obtained in step 3.3, in 5 ml of methanol, is 0.13 ml (0.76 mmol) of a 6N aqueous solution of sodium hydroxide. The mixture is heated at 60° C. for 30 minutes then poured into 100 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 residue obtained is recrystallized in acetonitrile in order to give 0.156 g of 2-(4-fluorophenyl)-6-[(3R)-3-methylpiperazin-1-yl]-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine after drying.

Workup

extractionThe product is extracted with dichloromethane
customThe organic phase is separated
dry with materialdried over sodium sulphate
customthe solvent is removed by evaporation under reduced pressure
customThe residue obtained
customis recrystallized in acetonitrile in order

Sources & evidence

ORD record: ord-57864d0a870548f3aff1f517b3020034
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546395B2

Reaction notes

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