2-Bromo-6-phenylcyclohexanone → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine

HRID 1803261

반응식

HRID 1803261 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.[Cl:15][C:16]1[N:17]=[CH:18][N:19]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH2:30])=[S:29])=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1>C(O)C.CCOC(C)=O>[Cl:15][C:16]1[N:17]=[CH:18][N:19]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]3[S:29][C:2]4[CH2:7][CH2:6][CH2:5][CH:4]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:3]=4[N:30]=3)=[CH:23][C:22]=2[O:31][CH3:32])[CH:20]=1

참가 물질

5

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 866498881-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea

생성물 1

HCID 58110069N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine수율 26%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-bromo-6-phenylcyclohexanone (89 mg, 0.352 mmol, from preparation AAA) and 1-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea (99 mg, 0.352 mmol, from step 4 of preparation A) was heated in ethanol (0.60 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 42 mg (26% yield) of the titled compound as a white solid. LC-MS (M+H)+ 437.0. 1H NMR (400 MHz, chloroform-d) δ ppm 7.50 (d, J=1.51 Hz, 1 H) 7.45 (d, J=2.52 Hz, 1 H) 7.28-7.36 (m, 2 H) 7.14-7.23 (m, 3H) 7.08 (d, J=8.31 Hz, 1 H) 7.00 (d, J=1.51 Hz, 1 H) 6.60 (dd, J=8.44, 2.39 Hz, 1 H) 4.05 (t, J=6.30 Hz, 1H) 3.47 (s, 3 H) 2.68-2.89 (m, 2 H) 2.20-2.28 (m, 1 H) 1.98 (dd, J=7.30, 5.29 Hz, 1 H) 1.78-1.93 (m, 2 H).

후처리

  1. customfrom step 4 of preparation A)
  2. customThe crude reaction
  3. washwashed with saturated sodium bicarbonate solution
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe crude product was purified

출처 및 근거

ORD 기록
ord-3cee49f658c345d3b3b0ef7a4d9fc464
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

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