Sodium Iodide → 3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamide

HRID 1878438Notes

Reaction equation

HRID 1878438 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:16].Cl[CH2:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=1)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]1[CH2:29][CH2:28]1)[CH3:26])=[O:23].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:18][C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=3)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]3[CH2:29][CH2:28]3)[CH3:26])=[O:23])[CH2:14][CH2:15]2)=[O:9])=[CH:4][C:3]=1[F:16]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 63187976(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanoneHCID 66878470HCID 66878470, compound

Product 1

HCID 579176753-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamideYield 15.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanone (2.74 mmol, 0.612 g), 3-(chloromethyl)-N-(1-cyano-1-cyclopropylethyl)benzamide (2.74 mmol, 0.72 g), sodium iodide (0.548 mmol, 0.082 g) and potassium carbonate (8.22 mmol, 1.136 g) were combined in acetonitrile (25 mL) and heated to reflux for 2 hours. The reaction was concentrated under reduced pressure and the resulting residue taken up in dichloromethane and washed with water. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane) to afford the title compound (195 mg). MS (ESI) m/z 450.3 [M+H]+

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane)

Sources & evidence

ORD record
ord-152cba8e56a9490eb5b0a956bdb1b975
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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