1,2-Dichloroethane → 6-((3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023170노트

반응식

HRID 1023170 반응식
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14]([OH:16])=O)[CH:8]=2)[NH:3]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[Cl:40][C:41]1[CH:42]=[C:43]([NH:48]/[C:49](/[NH2:52])=[N:50]/O)[CH:44]=[CH:45][C:46]=1[Cl:47].S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[Cl:40][C:41]1[CH:42]=[C:43]([NH:48][C:49]2[N:52]=[C:14]([CH2:13][O:12][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:11][CH2:10]4)[O:16][N:50]=2)[CH:44]=[CH:45][C:46]=1[Cl:47]

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 24436Sodium SulfateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 128192822-[(2-Oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetic acidHCID 178513435HCID 178513435, 화합물

생성물 1

HCID 866804126-((3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one수율 7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

To a stirred solution of 2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetic acid (0.15 g, 0.67 mmol) were added HOBt (0.1 g, 0.74 mmol), EDC (0.15 g, 0.74 mmol) and DIPEA (0.22 g, 1.69 mmol). The resulting reaction mixture was stirred at room temperature for 30 min. (E)-1-(3,4-dichlorophenyl)-2-hydroxyguanidine (0.15 g, 0.67 mmol) in DMF was added to the above reaction mixture followed by sodium sulfate (0.48 g, 3.39 mmol) and the reaction mixture was heated at 110° C. for 12 h. The reaction mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated. Purification was by preparative HPLC to give 6-((3-(3,4-dichlorophenylamino)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (9.3 mg, 7%). 1HNMR: 400 MHz, DMSO-d6: δ 2.42 (q, J=7.20 Hz, 2H), 2.85 (t, J=7.60 Hz, 2H), 5.41 (s, 2H), 6.78-6.87 (m, 2H), 6.94 (d, J=2.40 Hz, 1H), 7.41 (dd, J=2.80, 8.80 Hz, 1H), 7.59 (d, J=8.80 Hz, 1H), 7.71 (d, J=2.80 Hz, 1H), 9.96 (s, 1H), 10.39 (s, 1H). LCMS, RT 1.880 min; LCMS (ES-API), m/z 405.1.

후처리

  1. customThe resulting reaction mixture
  2. additionwas added to the above reaction mixture
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification

출처 및 근거

ORD 기록
ord-9600dd11771c420cb0376479cf421978
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722670B2

반응 노트

불러오는 중…