Methanesulfonyl chloride → HCID 19872048, compound

HRID 329364Notes

Reaction equation

HRID 329364 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:31]=[CH:30][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=3[O:27][CH3:28])[CH2:14][CH2:15][C:9]=2[CH:8]=1>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:31]=[CH:30][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]3[CH:25]=[CH:24][C:23]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:22][C:21]=3[O:27][CH3:28])[CH2:14][CH2:15][C:9]=2[CH:8]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 19872041HCID 19872041, compound

Product 1

HCID 19872048HCID 19872048, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Methanesulphonyl chloride (0.155 ml) was added dropwise to a solution of 7-amino-3-[2-(4-amino-2-methoxybenzamido)ethyl]-1,2,4,5-tetrahydro-3H-3-benzazepine in pyridine cooled to 0°, and the reaction mixture was stirred for a further 18 hours at room temperature. The solvent was evaporated in vacuo and the residue taken up in methylene chloride, washed three times with aqueous sodium bicarbonate and three times with brine. The organic layer was dried (Na2SO4), filtered and evaporated to give an oil, in which thin layer chromatography detected the presence of some unreacted starting material. The oil was therefore taken up in pyridine and treated with methanesulphonyl chloride (0.05 ml), and the reaction mixture was stirred at room temperature for 72 hours. The solvent was then evaporated in vacuo and the residue taken up in methylene chloride, washed three times with aqueous sodium bicarbonate and three times with brine. The organic layer was dried (Na2SO4), filtered and evaporated to give an oil. The resulting oil was then purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 5%) and the product-containing fractions were combined and evaporated in vacuo to give the title compound as a colourless foam, yield 0.32 g.

Workup

  1. temperaturecooled to 0°
  2. customThe solvent was evaporated in vacuo
  3. washwashed three times with aqueous sodium bicarbonate and three times with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil
  8. stirringthe reaction mixture was stirred at room temperature for 72 hours
  9. customThe solvent was then evaporated in vacuo
  10. washwashed three times with aqueous sodium bicarbonate and three times with brine
  11. dry with materialThe organic layer was dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated
  14. customto give an oil
  15. customThe resulting oil was then purified by column chromatography on silica eluting with methylene chloride
  16. additioncontaining methanol (0% up to 5%)
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd8e59273c3549109cb71e833ac7554c
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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