4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → HCID 117614418, compound

HRID 1465794Notes

Reaction equation

HRID 1465794 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]#[N:19])[CH:12]=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]=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([C:18]#[N:19])[CH:12]=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 89525152HCID 89525152, compound

Product 1

HCID 117614418HCID 117614418, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-(2-oxopiperazin-1-yl)quinoline-7-carbonitrile [I-4] (17 mg, 0.067 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (19 mg, 0.10 mmol) in EtOH (1.5 mL) in a 5 mL microwave tube was heated to 140° C. for 1 hour. 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): 443 [M+1]+.

Sources & evidence

ORD record
ord-7fc48549f97c46218959557a4c332d17
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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