Pyridine → HCID 86585942、化合物

HRID 51962

反応式

HRID 51962 の反応式
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]([NH:37][C:38]([C:40]1[CH:41]=[N:42][C:43]2[C:48]([CH:49]=1)=[CH:47][CH:46]=[C:45]([NH2:50])[CH:44]=2)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.N1C=CC=CC=1>CN(C)C=O.C(Cl)(Cl)Cl>[N:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH:30]([NH:37][C:38]([C:40]1[CH:41]=[N:42][C:43]2[C:48]([CH:49]=1)=[CH:47][CH:46]=[C:45]([NH:50][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:44]=2)=[O:39])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 964395HCID 964395、化合物HCID 865859407-Amino-quinoline-3-carboxylic acid (di-pyridin-2-yl-methyl)-amide

生成物 1

HCID 86585942HCID 86585942、化合物収率 34%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6212Chloroform溶媒

実験手順

A mixture of 2-benzyloxy-3-methoxybenzoic acid (109 mg, 0.42 mmol), thionyl chloride (5 ml) and 1 drop dimethylformamide was heated under reflux for 2 hr. The thionyl chloride was removed in vacuo, with traces being removed by adding methylene chloride and concentrating the solution in vacuo. The resulting 2-benzyloxy-3-methoxybenzoyl chloride was dissolved in chloroform and the solution was added dropwise to a solution of 7-amino-quinoline-3-carboxylic acid (di-pyridin-2-yl-methyl)-amide (75 mg, 0.21 mmol), 4-(N,N-dimethylaminopyridine) (DIMAP) (3 mg, 0.02 mmol) and pyridine (0.068 ml, 0.84 mmol) in chloroform at room temperature. The resulting solution was heated under reflux for 3 hr, then cooled to room temperature and concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue (960 mg) was purified by column chromatography on silica gel, eluting with 98:2 chloroform/methanol to yield the title compound as a solid (40.3 mg, 34% yield).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. customThe thionyl chloride was removed in vacuo, with traces
  4. custombeing removed
  5. additionby adding methylene chloride
  6. concentrationconcentrating the solution in vacuo
  7. dissolutionThe resulting 2-benzyloxy-3-methoxybenzoyl chloride was dissolved in chloroform
  8. temperatureThe resulting solution was heated
  9. temperatureunder reflux for 3 hr
  10. concentrationconcentrated to dryness in vacuo
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. washwashed sequentially with water and brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated to dryness in vacuo
  15. customThe residue (960 mg) was purified by column chromatography on silica gel
  16. washeluting with 98:2 chloroform/methanol

出典と根拠

ORDレコード
ord-7c6d04060e1e4a2cb55986e17a5d12d7
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

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