1-Methyl-4-(piperidin-4-yl)piperazine → HCID 178434420, compound

HRID 336852Notes

Reaction equation

HRID 336852 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[C:12]([C:13]#[N:14])=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=3[F:22])[N:10]=[C:9]3[NH:23][N:24]=[C:25]([CH3:26])[C:8]=23)=[CH:4][CH:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:30][CH2:29]1>O1CCOCC1>[F:22][C:16]1[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:15]=1[C:11]1[N:10]=[C:9]2[NH:23][N:24]=[C:25]([CH3:26])[C:8]2=[C:7]([C:5]2[O:6][C:2]([N:37]3[CH2:36][CH2:35][CH:34]([N:31]4[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]4)[CH2:39][CH2:38]3)=[CH:3][CH:4]=2)[C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 178434419HCID 178434419, compound

Product 1

HCID 178434420HCID 178434420, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.80 g (1.9 mmol) of 4-(5-bromofuran-2-yl)-6-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and 3.56 g (19.4 mmol) of 1-methyl-4-(piperidin-4-yl)piperazine in 55 ml of anhydrous dioxane is refluxed for 7 days. The mixture is concentrated and the residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%) to yield 0.51 g (51%) of 6-(2-fluoro-4-hydroxyphenyl)-3-methyl-4-(5-(4-(4-methylpiperazine-1-yl)piperidin-1-yl)furan-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of an orange solid.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%)

Sources & evidence

ORD record
ord-d6c048f7c7e942ec9e1ac1de242883d7
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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