Ethanesulfonyl chloride → HCID 18512117, compound

HRID 1370779Notes

Reaction equation

HRID 1370779 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[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.[CH2:24]([S:26](Cl)(=[O:28])=[O:27])[CH3:25]>N1C=CC=CC=1>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[C:10]([CH3:16])=[C:11]([NH:15][S:26]([CH2:24][CH3:25])(=[O:28])=[O:27])[CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 86586222HCID 86586222, compound

Product 1

HCID 18512117HCID 18512117, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 2B (0.03 g, 0.1 mmoles) in pyridine (2 mL) at 0° C. was treated with ethanesulfonyl chloride (0.01 g, 0.12 mmoles). The reaction mixture was quenched after 1 hour with water (2 mL), extracted with diethyl ether (5 mL), washed with water (2×2 mL), rinsed with brine (2 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ1.22 (t, 3H, J=7.3 Hz), 2.40 (s, 3H), 3.02 (dd, 2H, J=14.6, 7.5 Hz), 4.05 (s, 4H), 6.94 (m, 2H), 7.01 (m, 1H), 7.20 (m, 2H), 7.27 (m, 7H), 8.92 (s, 1H); MS (APCI+) m/z 395 (M+H)+.

Workup

  1. customThe reaction mixture was quenched after 1 hour with water (2 mL)
  2. extractionextracted with diethyl ether (5 mL)
  3. washwashed with water (2×2 mL)
  4. washrinsed with brine (2 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-99c06899de2a43349fe19ec15e4f17c6
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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