Methanesulfonyl chloride → HCID 69198619, compound

HRID 404922Notes

Reaction equation

HRID 404922 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[S:13][C:14]([CH:17]=[N:18]O)=[CH:15][N:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CS(Cl)(=O)=O>N1C=CC=CC=1.ClCCl>[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131731608HCID 131731608, compound

Product 1

HCID 69198619HCID 69198619, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 0° C. solution of Example 68E (464 mg, 1.66 mmol) in pyridine (10 mL) was added methanesulfonyl chloride (0.53 mL, 6.64 mmol). The reaction was warmed to 25° C., stirred for 4 hours and diluted with dichloromethane (50 mL). The mixture was washed with 10% HCl (2×50 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 20% ethyl acetate in hexanes to provide 363 mg of the title compound (84%) as a off-white solid, 1H NMR (300 MHz, DMSO-d6) δ ppm 1.31 (d, J=6.25 Hz, 6H) 5.14-5.30 (m, 1H) 6.89 (d, J=9.19 Hz, 1H) 7.87 (dd, J=9.01, 3.13 Hz, 1H) 8.23 (s, 1 H) 8.31 (d, J=2.57 Hz, 1H); MS (ESI) m/z 262.0 (M+H)+.

Workup

  1. washThe mixture was washed with 10% HCl (2×50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-66147cfd6d1e4f108629ab8381a857ba
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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