N-[2-butyl-3-{4-[2-cyanoethoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide → N-[2-butyl-3-{4-[(3-amino)propoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide

HRID 705440Notes

Reaction equation

[CH2:1]([C:5]1[O:6][C:7]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][C:8]=2[C:9]=1[C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]#[N:21])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]>CO.[Ni]>[CH2:1]([C:5]1[O:6][C:7]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:23][C:8]=2[C:9]=1[C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

3.0 g of N-[2-butyl-3-{4-[2-cyanoethoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide (IV) is dissolved in 300 ml of methanol and 5 g of Raney-Ni catalyst is added. The mixture is stirred at 25° C. at 10 bar H2 pressure for 24 hours. The catalyst is filtered, and the solvent is evaporated.

Workup

filtrationThe catalyst is filtered
customthe solvent is evaporated

Sources & evidence

ORD record: ord-894e23c40a4f4589840c0a3566317d44
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174959B2

Reaction notes

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