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

HRID 1023170ノート

反応式

HRID 1023170 の反応式
[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]

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9600dd11771c420cb0376479cf421978
出典データセット
uspto-grants-2014_05
特許番号
US08722670B2

反応ノート

読み込み中…