Sodium Iodide → HCID 58869183, compound

HRID 2355223Notes

Reaction equation

HRID 2355223 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH2:22])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:24][C:25]([NH:27][CH3:28])=[O:26].C(N(CC)CC)C.[Na+].[I-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:22][CH2:24][C:25]([NH:27][CH3:28])=[O:26])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 667732-chloro-N-methylacetamideHCID 58869130HCID 58869130, compound

Product 1

HCID 58869183HCID 58869183, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of C—[(R)-7-(3-Fluoro-benzenesulfonyl)-chroman-2-yl]-methylamine (0.07 g, 0.22 mmol) and 2-chloro-N-methylacetamide (0.023 g, 0.22 mmol) in dry DMF (3 mL) in a sealable tube was added triethylamine (0.1 mL, 0.72 mmol) and NaI (0.01 g). The tube was sealed and heated for four hours at 80° C., then cooled and quenched by addition of water. The reaction mixture was extracted EtOAc, and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered and contrated under reduced pressure. Purification of the residue by flash chromatography (EtOAc:MeOH 99:1 to 97:3) gave 0.044 g of 2-{[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-amino}-N-methyl-acetamide as a foam. MS (M+H)=393.

Workup

  1. customThe tube was sealed
  2. temperaturecooled
  3. customquenched by addition of water
  4. extractionThe reaction mixture was extracted EtOAc
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customPurification of the residue by flash chromatography (EtOAc:MeOH 99:1 to 97:3)

Sources & evidence

ORD record
ord-5e14a024d52647e7b159d574926ea36a
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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