4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 6-Fluoro-3-({4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}acetyl)-2-methylbenzonitrile

HRID 1466176Notes

Reaction equation

HRID 1466176 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11](=[O:20])[CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]2=[O:19])=[CH:4][CH:3]=1.[CH3:21][C:22]1[C:30]2[CH2:29][O:28][C:27](=[O:31])[C:26]=2[CH:25]=[CH:24][C:23]=1[C@@H:32]1[CH2:34][O:33]1>CCO>[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11](=[O:20])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:34][C@H:32]([OH:33])[C:23]3[CH:24]=[CH:25][C:26]4[C:27](=[O:31])[O:28][CH2:29][C:30]=4[C:22]=3[CH3:21])[CH2:15][C:14]2=[O:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 895251166-Fluoro-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile

Product 1

HCID 1175995336-Fluoro-3-({4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}acetyl)-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-Fluoro-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile (40 mg, 0.14 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (42 mg, 0.22 mmol) in EtOH (2 mL) was heated to 140° C. for 1 hour. The reaction mixture was concentrated to dryness, and dissolved in MeOH, filtered and shot into Mass-directed HPLC for separation to give the title product. LC-MS (IE, m/z): 466 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in MeOH
  3. filtrationfiltered
  4. customshot into Mass-directed HPLC for separation

Sources & evidence

ORD record
ord-926f5ba4df18494193932964f8208a32
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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