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

HRID 2265182

반응식

HRID 2265182 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-249a7dde4624468da5025f0d40e5365e
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855292B2

연결된 노트

불러오는 중…