Pyridine → HCID 86585942, 화합물

HRID 841825

반응식

HRID 841825 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86585942HCID 86585942, 화합물수율 34%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d53ac1cdca504b87a9b25e5bf200ceec
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369075B1

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