Piperidine → N-butyl-2,3-difluoro-N-[1-(4-piperidin-1-yl-but-2-enyl)-1H-benzoimidazol-2-ylmethyl]-benzamide

HRID 1071455Notes

Reaction equation

[F:1][C:2]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([N:6]([CH2:22][CH2:23][CH2:24][CH3:25])[CH:7](CC=CCCl)[C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1)=[O:5].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.CN1CCOCC1>[CH2:22]([N:6]([CH2:7][C:8]1[N:9]([CH2:29][CH:2]=[CH:3][CH2:4][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1)[C:4](=[O:5])[C:3]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:2]=1[F:1])[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 90 °C

Procedure

2,3-Difluoro-N-butyl-N-[(4-chlorobut-2-enyl)-1H-benzoimidazol-2-ylmethyl)-benzamide (26 mg, 0.06 mmol) was dissolved in 0.3 mL toluene. Piperidine (10 μL, 0.1 mmol) dissolved in 0.5 mL 95/5 toluene/4-methylmorpholine was added and the reaction mixture was heated at 90° C. for 15 hours. The reaction mixture was cooled to room temperature and deposited on a 1 g silica SPE column. The column was washed with 4 mL ethyl acetate to remove impurities followed by 4 mL 10/2/1 ethyl acetate/methanol/triethylamine to elute the product to afford 24 mg N-butyl-2,3-difluoro-N-[1-(4-piperidin-1-yl-but-2-enyl)-1H-benzoimidazol-2-ylmethyl]-benzamide.

Workup

additionwas added
temperatureThe reaction mixture was cooled to room temperature
washThe column was washed with 4 mL ethyl acetate
customto remove impurities
washto elute the product

Sources & evidence

ORD record: ord-17c313b2c2d44b938d873751fce20cd1
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906075B2

Reaction notes

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