Water → HCID 18789977, compound

HRID 1106887Notes

Reaction equation

HRID 1106887 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:12]([CH3:14])[CH3:13])=[C:6]([N:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)[CH:5]=1)([O-])=O.[H][H].[CH3:36][S:37]([Cl:40])(=[O:39])=[O:38].O>C(OCC)(=O)C.CO.[Pd]>[ClH:40].[CH3:36][S:37]([NH:1][C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:12]([CH3:14])[CH3:13])=[C:6]([N:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)[CH:5]=1)(=[O:39])=[O:38]

Participants

8

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 18789864HCID 18789864, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18789977HCID 18789977, compoundYield 26.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-Nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g, 1.98 mmol) was dissolved in 50 ml of a 1:1 solvent system of ethyl acetate and methanol; following 10% Pd/C (0.4 g), the solution was stirred at room temperature for 1 h as hydrogen gas was introduced. Thereafter, the reaction solution was filtered through Celite and the solvent was evaporated; the resulting residue (0.7 g) was dissolved in pyridine (20 ml) and, thereafter, the solution was cooled to 0° C. and methanesulfonyl chloride (0.19 ml, 2.5 mmol) was slowly added dropwise and the mixture was stirred at room temperature for 2 h; thereafter, water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated; the residue was dissolved in methanol (10 ml); after cooling to 0° C., a solution of 1N HCl (0.15 ml) saturated with ethyl ether was added and the mixture was stirred for 20 min to effect evaporation and thereby yield the titled compound 1-[4-methanesulfonamido-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane hydrochloride (0.28 g).

Workup

  1. additionwas introduced
  2. filtrationThereafter, the reaction solution was filtered through Celite
  3. customthe solvent was evaporated
  4. dissolutionthe resulting residue (0.7 g) was dissolved in pyridine (20 ml)
  5. extractionextraction
  6. dry with materialThe extracted organic layer was dried with magnesium sulfate
  7. customthe solvent was evaporated
  8. customthe resulting residue was purified
  9. additionThe fractions containing the product
  10. customwere collected
  11. customthe solvent was evaporated
  12. dissolutionthe residue was dissolved in methanol (10 ml)
  13. temperatureafter cooling to 0° C.
  14. additiona solution of 1N HCl (0.15 ml) saturated with ethyl ether was added
  15. stirringthe mixture was stirred for 20 min
  16. customevaporation

Sources & evidence

ORD record
ord-bba7050fbc0f4a4db2fe2aa3f3987c99
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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