5-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one → 6-Fluoro-3-(1-hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-methylbenzonitrile

HRID 1474374Notes

Reaction equation

HRID 1474374 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([CH:11]2[CH2:13][O:12]2)=[CH:4][CH:3]=1.[OH:14][CH:15]([C:23]1[CH:32]=[CH:31][C:26]2[C:27](=[O:30])[O:28][CH2:29][C:25]=2[C:24]=1[CH3:33])[CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CCO>[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([CH:11]([OH:12])[CH2:13][N:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH:15]([OH:14])[C:23]3[CH:32]=[CH:31][C:26]4[C:27](=[O:30])[O:28][CH2:29][C:25]=4[C:24]=3[CH3:33])[CH2:18][CH2:19]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 595687245-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-oneHCID 866473076-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

Product 1

HCID 498004726-Fluoro-3-(1-hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Fluoro-2-methyl-3-oxiran-2-ylbenzonitrile (69.2 mg, 0.391 mmol), 5-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one (54.0 mg, 0.195 mmol) was dissolved in EtOH (5 ml) then microwaved at 150° C. for 1 hr. Evaporated off ethanol and the residue was purified by mass directed hplc to yield 6-fluoro-3-(1-hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-methylbenzonitrile.

Workup

  1. customthen microwaved at 150° C. for 1 hr
  2. customEvaporated off ethanol
  3. customthe residue was purified by mass

Sources & evidence

ORD record
ord-0d2cad5232504db89716d25ad2ae1c8d
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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