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}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466174Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-methyl-5-(oxiran-2-yl)-2-benzofuran-1 (3H)-one (22 mg, 0.12 mmol) and 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (30 mg, 0.12 mmol) in EtOH (2 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 separation to give the title product. LC-MS (IE, m/z): 446 [M+1]+.

Workup

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

Sources & evidence

ORD record: ord-c21c749cd0d54ef9aed8383a0503aa40
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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