2-Bromo-6-phenylcyclohexanone → (3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2075974

반응식

HRID 2075974 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15]([NH2:17])=[S:16])[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1.Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15]2[S:16][C:27]3[CH2:28][CH2:29][CH2:30][CH:25]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:19][CH:20]=4)[C:26]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1

참가 물질

4

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 22459682(3-Methoxy-4-oxazol-5-yl-phenyl)-thiourea

생성물 1

HCID 57780726(3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine수율 83.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of (3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (74.8 mg, 0.3 mmol) and of 2-bromo-6-phenyl-cyclohexanone (75.9 mg, 0.3 mmol, preparation: WO9404487) in ethanol (4 mL) was heated over night to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (101 mg, 83%) as an off-white foam. MS ISP (m/e): 404.5 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.29 (s, 1H), 8.31 (s, 1H), 7.66 (s, 1H), 7.50 (d, 1H), 7.46-7.51 (m, 3H), 7.09-7.31 (m, 3H), 6.83 (s, 1H), 4.00 (m, 1H), 3.46 (s, 3H), 2.73 (m, 2H), 2.12 (m, 1H), 1.70-1.94 (m, 3H).

후처리

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified on silica gel

출처 및 근거

ORD 기록
ord-f7d6574307724d029c3157fc7e6614fe
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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