Methanesulfonyl chloride → HCID 15293135, compound

HRID 2210794Notes

Reaction equation

HRID 2210794 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:25]=[CH:26][C:27]([NH:29][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:28][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15293134HCID 15293134, compound

Product 1

HCID 15293135HCID 15293135, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of the title compound of Example 13 (1.0 g) in pyridine (15 mL) under nitrogen at approximately 5° C. (ice water bath) was added dropwise via syringe methanesulfonyl chloride (0.28 mL). The ice bath was removed, and the reaction was stirred at ambient temperature for 2 hours. The reaction was then evaporated under vacuum, and the residue was treated with 1M HCl. The insoluble product was collected by filtration, washed twice with 1M HCl, and then with water. The solid was suspended in methanol, heated to reflux on a steam bath, cooled to room temperature, and the product was collected by filtration. Recrystallization from acetonitrile yielded the title compound as a pinkish solid. Mp: 211°-212° C.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was then evaporated under vacuum
  3. additionthe residue was treated with 1M HCl
  4. filtrationThe insoluble product was collected by filtration
  5. washwashed twice with 1M HCl
  6. temperatureheated
  7. temperatureto reflux on a steam bath
  8. temperaturecooled to room temperature
  9. filtrationthe product was collected by filtration
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-7259bce80c404a318f750609a0243e84
Source dataset
uspto-grants-1995_10
Patent number
US05461046

Reaction notes

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