Pyridine → Quinoline carboxamide derivative 1

HRID 1259845

반응식

HRID 1259845 반응식
[C:1]1([C:7]2[CH:16]=[C:15]([C:17](Cl)=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[NH2:26][C:27]1[O:28][C:29]([C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)=[N:30][N:31]=1>CO>[O:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[C:29]1[O:28][C:27]([NH:26][C:17]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:16]=2)=[O:18])=[N:31][N:30]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 27604092-Phenylquinoline-4-carbonyl chloride

생성물 1

HCID 4253236Quinoline carboxamide derivative 1수율 43.1%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

2-phenyl-4-quinolinecarbonyl chloride (2.00 g, 7.47 mmol) was added in small portions to a pyridine (40 mL) solution of commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (1.69 g, 11.2 mmol), and the mixture was heated with stirring at 60° C. for 6 hours. To the reaction solution, methanol was added, and the solvent was distilled off. The obtained residue was triturated by the addition of water. The deposited crystal was collected by filtration, washed with methanol and then with ethyl acetate, and then recrystallized from DMF-methanol to obtain the title compound (1.23 g, 3.22 mmol) as a light brown powder (yield: 43%).

후처리

  1. temperaturethe mixture was heated
  2. distillationthe solvent was distilled off
  3. customThe obtained residue was triturated by the addition of water
  4. filtrationThe deposited crystal was collected by filtration
  5. washwashed with methanol
  6. customwith ethyl acetate, and then recrystallized from DMF-methanol

출처 및 근거

ORD 기록
ord-ee5b437691344d60bdb8eed564e0619d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466290B2

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