Acetic Acid → 7-(4-(2-(4-Cyanopyridin-2-yl)ethyl)piperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

HRID 535655Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

The compound was prepared according to the procedure disclosed in Example 39 starting from of 2-vinylisonicotinonitrile (0.076 g, 0.59 mmol), N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide (0.080 g, 0.29 mmol) (Example 39d), and acetic acid (0.013 mL, 0.23 mmol). Ethanol was used as solvent and the reaction heated at 90° C. for two days. The crude product was purified by preparative HPLC to give the title compound. Yield: 0.061 g (52%).

Workup

customThe compound was prepared
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-72ef4e0cae6e4bc0a9900e2dd2eb0a25
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859534B2

Reaction notes

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