Benzenesulfonyl chloride → HCID 11581951, compound

HRID 901212Notes

Reaction equation

HRID 901212 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:19].CCN(C(C)C)C(C)C.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC#N.O>[CH2:12]([N:4]1[C:5]2[C:10](=[CH:9][N:8]=[CH:7][CH:6]=2)[CH2:11][CH:2]([NH:1][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])[C:3]1=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58670142HCID 58670142, compound

Product 1

HCID 11581951HCID 11581951, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1G (140 mg, 0.55 mmol) in CH3CN (4 mL) at RT was added DIPEA (153 μL, 0.88 mmol), followed by benzenesulfonyl chloride (84 μL, 0.66 mmol). After addition, the reaction was stirred at RT for 30 min. The reaction was diluted with H2O and extracted with EtOAc (20 mL×3). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel (12 g) column chromatography eluting with a gradient of EtOAc (20-100%) in hexane to give the title compound as a white solid (182 mg, 84%). LC/MS (method A): retention time=2.10 min, (M+H)+=394. 1H-NMR (DMSO6, 400 MHz): δ 8.25-8.36 (m, 3H), 7.85-7.90 (m, 2H), 7.52-7.70 (m, 3H), 7.15-7.30 (m, 5H), 6.93 (d, J=4 Hz, 1H), 5.04 (dd, J1=28.6 Hz, J2=16.3 Hz 2H), 4.35-4.46 (m, 1H), 2.90-3.15 (m, 2H).

Workup

  1. additionAfter addition
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe combined organics were washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel (12 g) column chromatography
  8. washeluting with a gradient of EtOAc (20-100%) in hexane

Sources & evidence

ORD record
ord-e376342d743948c99d919779720b256c
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Reaction notes

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