Dimethyl Sulfoxide → HCID 66864798, compound

HRID 251868Notes

Reaction equation

HRID 251868 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C@H:14]1[C:23]2[C:18](=[C:19]([Cl:25])[CH:20]=[C:21]([Cl:24])[CH:22]=2)[CH2:17][N:16]([CH3:26])[CH2:15]1)=[O:6].CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[ClH:1].[Cl:24][C:21]1[CH:22]=[C:23]2[C:18](=[C:19]([Cl:25])[CH:20]=1)[CH2:17][N:16]([CH3:26])[CH2:15][C@H:14]2[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]1[CH2:2][CH2:3][CH2:4][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 596828794-Chloro-N-[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-butyramide

Product 1

HCID 66864798HCID 66864798, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-N-[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-butyramide (249 mg) was dissolved in abs. DMSO (10 ml) and finely powdered and dried potassium carbonate (250 mg) was added. With exclusion of moisture, the mixture was stirred vigorously at room temperature for 4 h. After standing overnight, the reaction mixture was diluted with water (50 ml) and then extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with sodium hydrogencarbonate and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. The residue was dissolved in water/acetonitrile and adjusted to pH 2 with 0.1 N HCl. After freeze-drying overnight, the desired product (116 mg) was obtained as a white powder.

Workup

  1. waitAfter standing overnight
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by means of preparative HPLC
  7. customthe acetonitrile was removed on a rotary evaporator
  8. extractionextracted three times with ethyl acetate
  9. dry with materialAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
  10. filtrationwere filtered
  11. concentrationconcentrated to dryness
  12. dissolutionThe residue was dissolved in water/acetonitrile
  13. customAfter freeze-drying overnight

Sources & evidence

ORD record
ord-15bf0041e7444aaa8da87788dc675f14
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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