Methanesulfonyl chloride → HCID 24853167, compound

HRID 2245371Notes

Reaction equation

HRID 2245371 reaction equation
[CH3:1][C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH3:1][C:2]1[S:6]/[C:5](=[N:7]\[S:32]([CH3:31])(=[O:34])=[O:33])/[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=3[CH:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15451838HCID 15451838, compound

Product 1

HCID 24853167HCID 24853167, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The imine (Example 26A, 30 mg, 0.09 mmol) was dissolved in dichloromethane (1.5 mL). Diisopropylethylamine (31 μl, 0.18 mmol, 2 equiv.) was added followed by the methanesulfonyl chloride (0.1 mmol, 1.1 equiv.). The reaction was stirred at room temperature for 4 hours. The reaction mixture was passed through a Si-amine cartridge (1 g, 1.6 mmol/g) to remove the excess sulfonyl chloride and washed with additional dichloromethane. The resulting solution was dried, concentrated, and purified by reverse phase HPLC. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.24 (3H), 2.90-2.96 (3H), 7.31 (1H), 7.56 (1H), 7.68 (1H), 7.8 (1H); MS (ESI) m/z 398.9 (M+H)+.

Workup

  1. customto remove the excess sulfonyl chloride
  2. washwashed with additional dichloromethane
  3. customThe resulting solution was dried
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-6084fc16c881429bbc0a77e4491eb439
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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