Dimethylformamide → 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one

HRID 1466144Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]piperazin-2-one (54 mg, 0.22 mmol), 5-(2-Bromoethyl)-2-benzofuran-1(3H)-one (105 mg, 0.44 mol), Triethylamine (0.15 mL, 1.1 mmol), and DMF (1.5 mL) was heated to 60° C. for 24 hours. The reaction was diluted with EtOAc, washed with water and brine, dried over MgSO4, and purified by prep-TLC (5% MeOH in DCM) to deliver the title product. LC-MS (IE, m/z): 407 [M+1]+.

Workup

washwashed with water and brine
dry with materialdried over MgSO4
custompurified by prep-TLC (5% MeOH in DCM)

Sources & evidence

ORD record: ord-c57cace3171b47c0992b1ce7cd99b956
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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