Methanesulfonyl chloride → HCID 58938503, compound

HRID 1367640Notes

Reaction equation

HRID 1367640 reaction equation
[NH2:1][C:2]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:3]=1/[CH:4]=[CH:5]/[C:6]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14](=[O:22])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[CH3:28][O:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:3](/[CH:4]=[CH:5]/[C:6]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:22])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[C:2]=1[NH:1][S:30]([CH3:29])(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58938509HCID 58938509, compound

Product 1

HCID 58938503HCID 58938503, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 14 (123 mg, 0.333 mmol) and MsCl (260 μL, 3.33 mmol) in pyridine (20 mL) was heated to ˜70° C. under N2 for 2 days. The mixture was concentrated in vacuo, and the residue was dissolved in CHCl3, washed with 10% citric acid, dried and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc/DCM (5-20%) to give pure 15 as a white solid (125 mg, 84%). MS (APCI): m/z 448 (100%, [M+H]+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed with 10% citric acid
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. washeluting with EtOAc/DCM (5-20%)

Sources & evidence

ORD record
ord-8b57b4e4182d4d43a675e910bafba045
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

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