4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 2-{4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}-7-methylquinoline-6-carbonitrile

HRID 1465795Notes

Reaction equation

HRID 1465795 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]3=[O:18])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20].[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>[OH:33][C@H:32]([C:23]1[CH:24]=[CH:25][C:26]2[C:27](=[O:31])[O:28][CH2:29][C:30]=2[C:22]=1[CH3:21])[CH2:34][N:15]1[CH2:16][CH2:17][N:12]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([CH3:1])=[C:3]([C:19]#[N:20])[CH:4]=3)[N:9]=2)[C:13](=[O:18])[CH2:14]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 895251837-Methyl-2-(2-oxopiperazin-1-yl)quinoline-6-carbonitrile

Product 1

HCID 715257802-{4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}-7-methylquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 7-Methyl-2-(2-oxopiperazin-1-yl)quinoline-6-carbonitrile [I-3] (125 mg, 0.47 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (134 mg, 0.70 mmol) in EtOH (1.5 mL) in a 5 mL microwave tube was heated to 140° C. for 20 minutes. LC showed formation of the desired product, which was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 457 [M+1]+.

Sources & evidence

ORD record
ord-d83f7f5fe8124239bc9fa58b9c6039ac
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

Loading…