Potassium Carbonate → 7-(4-(2-(6-Methoxypyridin-2-yl)ethyl)piperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

HRID 383835Notes

Reaction equation

[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[O:6][C:7]2[C:13]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=[O:4].CC1C=CC(S(O[CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[N:35]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:41][O:40][C:36]1[N:35]=[C:34]([CH2:33][CH2:32][N:17]2[CH2:18][CH2:19][N:14]([C:13]3[C:7]4[O:6][C:5]([C:3]([N:2]([CH3:20])[CH3:1])=[O:4])=[CH:9][C:8]=4[CH:10]=[CH:11][CH:12]=3)[CH2:15][CH2:16]2)[CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A reaction mixture of N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide (0.090 g, 0.33 mmol) (Example 39d), 2-(6-methoxypyridin-2-yl)ethyl 4-methylbenzenesulfonate (0.10 g, 0.33 mmol) and potassium carbonate (0.046 g, 0.33 mmol) in dry acetonitrile (10 mL) was heated at 80° C. for over night. After cooling, the mixture was filtered and the solvent removed in vacuo. The product was purified by preparative HPLC to give the title compound. Yield: 0.048 g (36%).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered
customthe solvent removed in vacuo
customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-2d069d98923d4027ae5fde24d9917ef9
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367676B2

Reaction notes

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