Sodium Chloride → HCID 57471174, compound

HRID 510500Notes

Reaction equation

HRID 510500 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:28]C(=O)C(F)(F)F.I[CH3:40].[Na+].[Cl-]>CC(N(C)C)=O>[ClH:3].[NH2:28][CH:9]1[CH:8]([CH2:7][C:6]2[CH:35]=[CH:36][C:37]([Cl:38])=[C:4]([Cl:3])[CH:5]=2)[C:17]2[CH:16]=[C:15]([O:18][CH2:19][CH2:20][N:21]([CH3:40])[S:22]([CH2:25][CH2:26][CH3:27])(=[O:23])=[O:24])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57467198HCID 57467198, compound

Product 1

HCID 57471174HCID 57471174, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

NaH (3.38 mg, 0.078 mmol, 55% in oil) was suspended in DMA (5 ml) and N-(1-(3,4-dichlorobenzyl)-7-(2-(propylsulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl)-2,2,2-trifluoroacetamide (40 mg, 0.07 mmol) dissolved in DMA (4 ml) was added dropwise. After stirring for 1 h iodomethane (10.5 mg, 0.074 mmol) dissolved in DMA (1 ml) was added. After stirring for another 14 h the reaction mixture was added to a halfconcentrated solution of NaCl. Extraction with ethyl acetate, washing of the organic layers with water and saturated NaCl solution followed by drying with Na2SO4 gave a residue that was washed with diisopropyl ether. Cleavage of the amide bond was achieved by stirring the residue with concentrated NaOH in water and subsequent extraction with ethyl acetate. The organic layer was dried with MgSO4 and evaporated. The residue was purified by preparative HPLC (RP-18, acetonitrile/water, 0.01% TFA). After transferring the product into the HCl salt a yellow solid (11.0 mg, 0.021 mmol, 30%) was obtained.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. extractionExtraction with ethyl acetate
  4. washwashing of the organic layers with water and saturated NaCl solution
  5. dry with materialby drying with Na2SO4
  6. customgave a residue that
  7. washwas washed with diisopropyl ether
  8. stirringby stirring the residue
  9. extractionwith concentrated NaOH in water and subsequent extraction with ethyl acetate
  10. dry with materialThe organic layer was dried with MgSO4
  11. customevaporated
  12. customThe residue was purified by preparative HPLC (RP-18, acetonitrile/water, 0.01% TFA)
  13. customwas obtained

Sources & evidence

ORD record
ord-7d01e000118745e3898ffecf06f975a6
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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