Dimethylformamide → 6-{4-[2-(4-Cyanophenyl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466141Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+]([O-])=O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].[CH3:38][N:39](C=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:38]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][N:6]2[CH2:5][CH2:4][N:3]([CH:8]3[CH2:17][CH2:16][C:15]4[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=4[CH2:9]3)[C:2](=[O:1])[CH2:7]2)=[CH:24][CH:25]=1)#[N:39]

Participants

Conditions

Temperature: 50 °C

Procedure

To a flask charged with 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (30 mg, 0.12 mmol) and a stir bar was added 1-(2-Bromoethyl)-4-nitrobenzene (39 mg, 0.19 mmol), K2CO3 (69 mg, 0.50 mmol), Tetrabutylammonium Iodide (12 mg, 0.025 mmol), and DMF (1 mL). The mixture was heated to 50° C. for 16 hours. LC showed product formation. The desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 385 [M+1]+.

Workup

customThe desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA)

Sources & evidence

ORD record: ord-ef5cbad648ea4d5598c34bbdf8a9dbd3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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