Pyridine → 4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl ester

HRID 2265182Notes

Reaction equation

HRID 2265182 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:13]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([S:23](Cl)(=[O:25])=[O:24])[C:17]=2[N:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.C(Cl)Cl>CCOC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=1[NH:1][S:23]([C:18]1[C:17]2[N:16]=[CH:15][CH:14]=[N:13][C:22]=2[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 80001Methyl 4-chloroanthranilateHCID 16090697Quinoxaline-5-sulfonyl chloride

Product 1

HCID 671992924-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-amino-4-chlorobenzoate (0.33 g, 1.8 mmol), quinoxaline-5-sulfonyl chloride (0.40 g, 1.8 mmol), pyridine (0.71 mL, 8.8 mmol), and DCM (10 mL) was stirred at rt for 16 h. EtOAc (75 mL) was added and the solution was washed with satd. aq. NaHCO3 (50 mL), then dried and concentrated. Chromatographic purification of this residue (EtOAc/hexanes) gave the title compound as a white solid (0.60 mg, 90%). MS (ESI+): mass calcd. for C16H12ClN3O4S, 377.0; m/z found, 378 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.44 (s, 1H), 8.97 (d, J=1.8, 1H), 8.95 (d, J=1.8, 1H), 8.61 (dd, J=7.4, 1.4, 1H), 8.33 (dd, J=8.5, 1.4, 1H), 7.89 (dd, J=8.4, 1.0, 1H), 7.84 (d, J=2.0, 1H), 7.77 (d, J=8.6, 1H), 6.89 (dd, J=8.6, 2.0, 1H), 3.90 (s, 3H).

Workup

  1. washthe solution was washed with satd
  2. dry with materialaq. NaHCO3 (50 mL), then dried
  3. concentrationconcentrated
  4. customChromatographic purification of this residue (EtOAc/hexanes)

Sources & evidence

ORD record
ord-249a7dde4624468da5025f0d40e5365e
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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