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

HRID 1465786Notes

Reaction equation

HRID 1465786 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11]2.[CH3:20][C:21]1[C:29]2[CH2:28][O:27][C:26](=[O:30])[C:25]=2[CH:24]=[CH:23][C:22]=1[C@@H:31]1[CH2:33][O:32]1>CCO>[OH:32][C@H:31]([C:22]1[CH:23]=[CH:24][C:25]2[C:26](=[O:30])[O:27][CH2:28][C:29]=2[C:21]=1[CH3:20])[CH2:33][N:6]1[CH2:5][CH2:4][N:3]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11]3)[C:2](=[O:1])[CH2:7]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 895251936-(2-Oxopiperazin-1-yl)naphthalene-2-carbonitrile

Product 1

HCID 715257786-{4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}naphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
148 °C

Procedure

A mixture of 6-(2-Oxopiperazin-1-yl)naphthalene-2-carbonitrile (33 mg, 0.13 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (38 mg, 0.20 mmol) in EtOH (2 mL) in a 5 mL microwave tube was heated to 148° C. for 1.5 hours. LC showed formation of the title product, which was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 442 [M+1]+.

Sources & evidence

ORD record
ord-b6f42021d8c041fe8ce405167f80d386
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

Loading…