Sodium Iodide → Ethyl 3-{[(4-{[cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091432Notes

Reaction equation

HRID 2091432 reaction equation
Cl[CH:2]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=2[O:5][C:4]=1[CH3:14].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH3:38])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[CH:24][CH:23]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH:15]1([CH:2]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([N:30]([CH3:38])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[CH:26][CH:27]=2)[C:3]2[C:7]3[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=3[O:5][C:4]=2[CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 46941342Ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoateHCID 667772013-[Chloro(cyclohexyl)methyl]-6-methoxy-2-methyl-1-benzofuran

Product 1

HCID 66778831Ethyl 3-{[(4-{[cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-[chloro(cyclohexyl)methyl]-6-methoxy-2-methyl-1-benzofuran (530 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate (498 mg) synthesized in Example 2(2) and N,N-dimethylformamide (10 mL) were added sodium iodide (408 mg) and sodium carbonate (288 mg), and the mixture was stirred at 80° C. overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (781 mg, 85%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ccd4d9f9132b4d1db1e24a1b7fdb4bbf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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