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

HRID 1465787Notes

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:22]([CH:31]2[CH2:33][O:32]2)=[CH:23][C:24]2[CH2:28][O:27][C:26](=[O:29])[C:25]=2[CH:30]=1>CCO>[OH:32][CH:31]([C:22]1[C:21]([CH3:20])=[CH:30][C:25]2[C:26](=[O:29])[O:27][CH2:28][C:24]=2[CH:23]=1)[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

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-(2-Oxopiperazin-1-yl)naphthalene-2-carbonitrile [I-5] (40 mg, 0.16 mmol) and 6-methyl-5-(oxiran-2-yl)-2-benzofuran-1(3H)-one [I-16] (30 mg, 0.16 mmol of the fast eluting isomer) in EtOH (1.5 mL) was heated to 140° C. for 1 hour. The reaction mixture was concentrated to dryness, and dissolved in MeOH, filtered and shot into Mass-directed HPLC for purification to give the title product. LC-MS (IE, m/z): 442 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated to dryness
dissolutiondissolved in MeOH
filtrationfiltered
customshot into Mass-directed HPLC for purification

Sources & evidence

ORD record: ord-5b18995cbd2e43ba960ae132eed6e82a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999991B2

Reaction notes

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