Hydrochloric Acid → {4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

HRID 1715855ノート

反応式

HRID 1715855 の反応式
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)=[O:4].S(Cl)(Cl)=O.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([O:40][CH3:41])=[C:24]([S:26]([N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([NH2:39])[CH:37]=3)[CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])[CH:25]=1.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:12])[NH:39][C:36]2[CH:37]=[C:38]3[C:33]([CH2:32][CH2:31][CH2:30][N:29]3[S:26]([C:24]3[CH:25]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=3[O:40][CH3:41])(=[O:28])=[O:27])=[CH:34][CH:35]=2)=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 138161444-(2-Methoxy-2-oxoethyl)benzoic acidHCID 684327061-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

生成物 1

HCID 68434762{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

4-Methoxycarbonylmethyl-benzoic acid (52.00 mg, 0.27 mmol) was suspended in dichloromethane (2.00 mL) and treated with thionyl chloride (95.57 mg, 0.80 mmol). The mixture was stirred at 50° C. for 18 hours, and the volatiles were evaporated. The residue was redissolved in tetrahydrofuran (2.00 mL) and treated with 1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine (94.48 mg, 0.27 mmol) and 4-dimethylaminopyridine (66.76 mg, 0.54 mmol). The mixture was warmed to 75° C. and stirred for 2.5 hours. The mixture was treated with HCl 1 N and the slurry extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (dichloromethane/methanol gradient) to yield {4-[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester as an off-white solid, 134.20 mg (95%), MS (ISP): m/e=529.3 (M+H).

後処理

  1. customthe volatiles were evaporated
  2. dissolutionThe residue was redissolved in tetrahydrofuran (2.00 mL)
  3. temperatureThe mixture was warmed to 75° C.
  4. stirringstirred for 2.5 hours
  5. extractionthe slurry extracted several times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by flash chromatography (dichloromethane/methanol gradient)

出典と根拠

ORDレコード
ord-cfaf4664916749e98f4fb40b6508a1c4
出典データセット
uspto-grants-2010_09
特許番号
US07799933B2

反応ノート

読み込み中…