4-Toluenesulfonyl chloride → HCID 71541941, compound

HRID 1023198Notes

Reaction equation

HRID 1023198 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][NH:13][C:14](=O)[CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH:21]=[CH:20]3)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][C:10]1[O:11][C:14]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH:21]=[CH:20]3)=[N:13][N:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86680435HCID 86680435, compound

Product 1

HCID 71541941HCID 71541941, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3,4-dichlorophenyl)-N′-(2-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)acetyl)acetohydrazide (0.2 g, 0.476 mmol) and TEA (0.265 mL, 1.904 mmol) in DCM (8 mL) at 0° C., Ts-Cl (0.181 g, 0.952 mmol) was added. The resulting solution was stirred at room temperature overnight. The reaction mixture was concentrated and dissolved in ethyl acetate, then washed with 10% NaHCO3 solution and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to a yellow gum, which was further washed with diethyl ether and chloroform to afford a brown solid. The crude product was purified by preparative HPLC on a C18 reverse phase column (ACN-NH4OAc method) to afford 6-((5-(3,4-dichlorobenzyl)-1,3,4-oxadiazol-2-yl)methoxy)quinolin-2(1H)-one (0.015 g, 8%). 1H NMR: 400 MHZ, DMSO-d6: δ 4.38 (s, 2H), 5.40 (s, 2H), 6.51 (dd, J=2.00, 9.60 Hz, 1H), 7.25 (d, J=2.40 Hz, 2H), 7.34 (dd, J=2.00, 8.00 Hz, 2H), 7.62 (d, J=8.00 Hz, 1H), 7.65 (d, J=2.00 Hz, 1H), 7.81 (d, J=9.60 Hz, 1H), 11.68 (s, 1H). LCMS: RT 1.61 min. LCMS (ES-API), m/z 403.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with 10% NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to a yellow gum, which
  6. washwas further washed with diethyl ether and chloroform
  7. customto afford a brown solid
  8. customThe crude product was purified by preparative HPLC on a C18 reverse phase column (ACN-NH4OAc method)

Sources & evidence

ORD record
ord-5b0d875b348d48ee929473d8568523d9
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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