4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → HCID 89535477, compound

HRID 1465789Notes

Reaction equation

HRID 1465789 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([C:18]#[N:19])=[CH:15]2)=[CH:10][CH:9]=1.[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:17]=[C:16]3[C:11]([CH:12]=[CH:13][C:14]([C:18]#[N:19])=[CH:15]3)=[CH:10][CH:9]=2)[C:2](=[O:1])[CH2:7]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 89525191HCID 89525191, compound

Product 1

HCID 89535477HCID 89535477, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 7-(2-oxopiperazin-1-yl)naphthalene-2-carbonitrile [I-7] (35 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) in a 5 mL microwave tube was heated to 145° C. for 2 hours. LC showed formation of the title product, which was purified by silica gel flash chromatography. LC-MS (IE, m/z): 442 [M+1]+.

Sources & evidence

ORD record
ord-36cf9a2aaa844b958659f0ec74cb858b
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

Loading…