Sodium Iodide → N-tert-Butyl-3-((4-(3-fluoro-4-nitrobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)benzamide

HRID 1878390Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][F:20])[CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:21]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[CH:28]=1)([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.[I-].[Na+]>C(#N)C>[C:21]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][N:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[C:4]3[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=3)[CH2:14][CH:15]2[CH2:19][F:20])[CH:28]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred mixture of (3-fluoro-4-nitrophenyl)(3-(fluoromethyl)piperazin-1-yl)methanone (456 mg, 1.6 mmol), N-tert-butyl-3-(chloromethyl)benzamide (361 mg, 1.6 mmol), triethylamine (3.1 mmol, 341 mg) and sodium iodide (1.6 mmol, 240 mg) in acetonitrile (10 mL) was heated to 60° C. for several hours. The reaction was concentrated under reduced pressure. The residue was then dissolved in dichloromethane and extracted with water (×3). The organic phase was dried (sodium sulfate) and concentrated under vacuum. The crude material was purified using silica chromatography to give the title compound (435 mg). MS (ESI) m/z 475.7[M+H]+

Workup

concentrationThe reaction was concentrated under reduced pressure
dissolutionThe residue was then dissolved in dichloromethane
extractionextracted with water (×3)
dry with materialThe organic phase was dried (sodium sulfate)
concentrationconcentrated under vacuum
customThe crude material was purified

Sources & evidence

ORD record: ord-736fb81fe7f04add9513906cdd091f46
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314091B2

Reaction notes

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