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

HRID 1466175Notes

Reaction equation

HRID 1466175 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]#[N:10])=[C:7]([CH3:11])[C:6]([C:12](=[O:21])[CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]2=[O:20])=[CH:5][CH:4]=1.[CH3:22][C:23]1[C:31]2[CH2:30][O:29][C:28](=[O:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[C@@H:33]1[CH2:35][O:34]1>CCO>[OH:34][C@H:33]([C:24]1[CH:25]=[CH:26][C:27]2[C:28](=[O:32])[O:29][CH2:30][C:31]=2[C:23]=1[CH3:22])[CH2:35][N:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:12]([C:6]2[C:7]([CH3:11])=[C:8]([C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]#[N:10])=[O:21])[C:15](=[O:20])[CH2:16]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 895247776-Methoxy-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile

Product 1

HCID 1175993413-({4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}acetyl)-6-methoxy-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-Methoxy-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 (40 mg, 0.21 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): 478 [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-23a7f2b8e33c4ba6bf3fd372d82febcc
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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