2-Bromo-6-phenylcyclohexanone → HCID 46864322, 화합물

HRID 1803260

반응식

HRID 1803260 반응식
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:29][C:30]([NH2:32])=[S:31])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[N:26][C:25]([CH3:28])=[N:24]1>C(O)C.CCOC(C)=O>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:29][C:30]2[S:31][C:2]3[CH2:7][CH2:6][CH2:5][CH:4]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:3]=3[N:32]=2)[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[N:26][C:25]([CH3:28])=[N:24]1

참가 물질

5

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86649898HCID 86649898, 화합물

생성물 1

HCID 46864322HCID 46864322, 화합물수율 39%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-bromo-6-phenylcyclohexanone (84 mg, 0.332 mmol, from preparation AAA) and 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (87 mg, 0.332 mmol, from step 4 of preparation F) was heated in ethanol (0.55 mL) at 80° C. for 3 h. The crude reaction was diluted with EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo. The crude product was purified using preparatory TLC (60% acetone/hexanes) to give 54 mg (39% yield) of the titled compound as a white solid. LC-MS (M+H)+ 418.0. 1H NMR (400 MHz, chloroform-d) δ ppm 8.44 (s, 1 H) 7.49 (dd, J=5.41, 3.15 Hz, 2 H) 7.23-7.35 (m, 2 H) 7.12-7.21 (m, 3 H) 6.60 (dd, J=8.56, 2.27 Hz, 1H) 3.98-4.08 (m, 1 H) 3.49 (s, 3 H) 2.66-2.85 (m, 2 H) 2.46 (s, 3 H) 2.17-2.26 (m, 1 H) 1.92-2.05 (m, 1 H) 1.78-1.91 (m, 2 H).

후처리

  1. customThe crude reaction
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationThe organic layer was concentrated in vacuo
  4. customThe crude product was purified

출처 및 근거

ORD 기록
ord-75451273d3b04d6aa1661d0c9f4735ea
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

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