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

HRID 2265182

反応式

HRID 2265182 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-249a7dde4624468da5025f0d40e5365e
出典データセット
uspto-grants-2010_12
特許番号
US07855292B2

関連ノート

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