4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one → 5-(1-hydroxy-2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one

HRID 1474361Notes

Reaction equation

HRID 1474361 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:14][O:13]1.[CH3:15][C:16]1[C:24]2[CH2:23][O:22][C:21](=[O:25])[C:20]=2[CH:19]=[CH:18][C:17]=1[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(O)C>[OH:13][CH:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])[CH2:14][N:31]1[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:25])[O:22][CH2:23][C:24]=3[C:16]=2[CH3:15])[CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 595686884-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one

Product 1

HCID 498044785-(1-hydroxy-2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-yl}ethyl)-4-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (60 mg, 0.31 mmol, 1.2 mmol) and 4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one (68 mg, 0.26 mmol, 1.0 eq) were suspended in ethanol (5 ml) in a microwave tube. The tube was capped, degassed under vacuum, and purged with nitrogen gas. The mixture was heated to 150° C. for 30 min under microwave irradiation. The mixture was then concentrated and purified by flash column chromatography (0-10% MeOH/DCM).

Workup

  1. customThe tube was capped
  2. customdegassed under vacuum
  3. custompurged with nitrogen gas
  4. concentrationThe mixture was then concentrated
  5. custompurified by flash column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-04671f86f73244c8bc2d87c778c3a1d9
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

Loading…