Methanesulfonyl chloride → HCID 18511975, compound

HRID 1370785Notes

Reaction equation

HRID 1370785 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH2:1]([N:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:23]=1)[C:9]1[C:10]([CH3:16])=[C:11]([NH:15][S:29]([CH3:28])(=[O:31])=[O:30])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68858129HCID 68858129, compound

Product 1

HCID 18511975HCID 18511975, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude product from Example 6C in pyridine (8.8 mL) was treated with methanesulfonyl chloride (0.28 mL, 3.60 mmoles) at 0° C. The reaction mixture turned from clear and colorless to yellow. After 30 minutes, the mixture was quenched with water (5.0 mL) and was concentrated under reduced pressure. The residue was dissolved in diethyl ether (200 mL), washed with water (2×100 mL), brine (100 mL), dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 4:1→1:1 hexanes:ethyl acetate) to provide the title compound as a yellow solid (1.33 g, 83%). A small portion of the residue (0.1 g) was repurified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column. 1H NMR (300 MHz, CDCl3) δ7.92 (d, J=6.8 Hz, 2H), 7.21 (m, 8H), 7.11 (t, J=8.0 Hz, 1H), 6.89 (d, J=8.0 Hz, 1H), 6.11 (s, 1H), 4.12 (s, 2H), 4.05 (s, 2H), 3.90 (s, 3H), 2.95 (s, 3H), 2.34 (s, 3H); MS (APCI+) m/z 439 (M+H)+.

Workup

  1. customthe mixture was quenched with water (5.0 mL)
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether (200 mL)
  4. washwashed with water (2×100 mL), brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (silica gel, 4:1→1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-e3ac163143b644e4ba6e493d45dfe442
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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