Pyridine → N-[2-butyl-3-{4-[2-cyanoethoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide

HRID 705441Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][C:25]#[N:26])=[CH:18][CH:17]=3)=[O:15])[C:6]=2[CH:27]=1.N1C=CC=CC=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:27][C:6]=2[C:7]=1[C:14](=[O:15])[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][C:25]#[N:26])=[CH:20][CH:21]=1)[CH2:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: 32.5 °C

Procedure

4.0 g of (5-amino-2-butyl-benzofur-3-yl)-[4-(2-cyanoethoxy)phenyl]methanon (VI) is dissolved in 40 ml of dichloromethane. The mixture is warmed to 30-35° C. and 1.05 g of pyridine is added at this tempereature in 5 minutes. At this temperature 1.5 g of methane sulfonyl chloride is added in 5 minutes and the mixture is stirred at 30-35° C. for 3 hours: The mixture is cooled to 20° C. and washed with 2×15 ml of water, 2×15 ml of NaHCO3 of 5% and 1×15 ml of water. The phases are separated and the dichloromethane is evaporated.

Workup

temperatureThe mixture is cooled to 20° C.
washwashed with 2×15 ml of water, 2×15 ml of NaHCO3 of 5% and 1×15 ml of water
customThe phases are separated
customthe dichloromethane is evaporated

Sources & evidence

ORD record: ord-f7a900a13d5b4615a66c566397c90576
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174959B2

Reaction notes

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