Hydrochloric Acid → HCID 71542043, 화합물

HRID 1023177노트

반응식

HRID 1023177 반응식
[OH:1]/[N:2]=[C:3](/[NH2:17])\[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]#N)[CH:22]=[CH:23][C:24]=1[Cl:25].C(O)C.Cl>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]2[O:1][N:2]=[C:3]([CH2:4][O:5][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]4)[N:17]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6042543,4-DichlorophenylcyanamideHCID 28203387HCID 28203387, 화합물

생성물 1

HCID 71542043HCID 71542043, 화합물수율 7%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (E)-N′-hydroxy-2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetimidamide (0.1 g, 0.425 mmol) in ethyl acetate (10 mL) was added a 0.5M solution of zinc chloride (0.073 mL, 0.510 mmol) followed by N-(3,4-dichlorophenyl)cyanamide (0.080 g, 0.425 mmol) and stirred at room temperature for 12 h. Then reaction mixture was concentrated. Ethanol (10.00 mL) was added along with HCl (0.1 mL, 3.29 mmol) and the reaction mixture was heated at 80° C. for 6 h. The reaction mixture was concentrated and basified with sodium bicarbonate solution, then the resulting solid was filtered and was washed with acetonitrile to give 6-((5-((3,4-dichlorophenyl)amino)-1,2,4-oxadiazol-3-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one as a white solid (12 mg, 6.8% yield). 1H NMR 400 MHz, DMSO-d6: δ 2.41 (t, J=15.20 Hz, 2H), 2.84 (t, J=15.20 Hz, 2H), 4.94 (s, 2H), 6.77-6.79 (m, 1H), 6.84-6.87 (m, 1H), 6.93 (d, J=2.80 Hz, 1H), 7.30 (s, 1H), 7.37 (s, 1H), 7.80 (s, 1H), 9.91 (s, 1H). LCMS: RT 1.963 min; LCMS (ES-API), m/z 403.0 [M−H]−.

후처리

  1. customThen reaction mixture
  2. concentrationwas concentrated
  3. temperaturethe reaction mixture was heated at 80° C. for 6 h
  4. concentrationThe reaction mixture was concentrated
  5. filtrationthe resulting solid was filtered
  6. washwas washed with acetonitrile

출처 및 근거

ORD 기록
ord-5bc00b0c8f164dbdb39a6546eb9e35f9
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722670B2

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