Sodium Iodide → HCID 57917701, compound

HRID 1878387Notes

Reaction equation

HRID 1878387 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@@H:12]([CH:16]([CH3:18])[CH3:17])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:19].[C:20]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:32][C:28]3[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=3)[C:25]([NH:24][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:34])[C@@H:12]([CH:16]([CH3:17])[CH3:18])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 43156221N-tert-butyl-3-(chloromethyl)benzamideHCID 57917636HCID 57917636, compound

Product 1

HCID 57917701HCID 57917701, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-(4-Amino-3-fluorophenyl)(3-isopropylpiperazin-1-yl)methanone (0.754 mmol, 200 mg), N-tert-butyl-3-(chloromethyl)benzamide (0,754 mmol, 170 mg), potassium carbonate (1.508 mmol, 208 mg) and sodium iodide (0.075 mmol, 11.30 mg) were dissolved in acetonitrile (20 mL) and heated at reflux for 3 hours. The reaction was concentrated under vacuum and the crude material dissolved in ethyl acetate and washed with water, dried over sodium sulphate and concentration under vacuum. The crude residue was then purified by column chromatography (eluting with dichloromethane to dichloromethane/methanol (1% to 5%)) to give the title compound (160 mg) as an off white solid. MS (ESI) m/z 456.4 [M+H]+

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction was concentrated under vacuum
  4. dissolutionthe crude material dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulphate and concentration under vacuum
  7. customThe crude residue was then purified by column chromatography (eluting with dichloromethane to dichloromethane/methanol (1% to 5%))

Sources & evidence

ORD record
ord-57502aaec10d45c281ba2c3cfd853e7c
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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