Sodium Iodide → HCID 57917599, compound

HRID 1878394Notes

Reaction equation

HRID 1878394 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][C:12]([CH3:17])([CH3:16])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:18].[C:19]([NH:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Cl)[CH:26]=1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.[I-].[Na+]>C(#N)C.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:31][C:27]3[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=3)[C:24]([NH:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:33])[C:12]([CH3:16])([CH3:17])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:18]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 43156221N-tert-butyl-3-(chloromethyl)benzamideHCID 66878299HCID 66878299, compound

Product 1

HCID 57917599HCID 57917599, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (4-amino-3-fluorophenyl)(3,3-dimethylpiperazin-1-yl)methanone (0.521 mmol, 131 mg) in acetonitrile (5.213 mL) was added N-tert-butyl-3-(chloromethyl)benzamide (0.573 mmol, 129 mg), and triethylamine (1.040 mmol, 145 μl, 105 mg). A catalytic amount of sodium iodide was added. The mixture was heated to reflux for 3 hours. The mixture was allowed to cool and ethyl acetate was added. The organic mixture was washed with water, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica chromatography (eluting with 5% methanol in dichloromethane) to yield the title compound (90 mg). MS (ESI) m/z 441.4 [M+H]+

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool
  4. washThe organic mixture was washed with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica chromatography (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-94603d2bf5ff427e975b382a444477f4
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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