Methanesulfonyl chloride → HCID 15293135, compound

HRID 1464442Notes

Reaction equation

HRID 1464442 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 1 M HCl. The insoluble product was collected by filtration, washed twice with 1 M 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 1 M HCl
  4. filtrationThe insoluble product was collected by filtration
  5. washwashed twice with 1 M 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-a9e27ee0aa9a4d6ca9fd13a2d1f3a841
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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