2-Bromo-6-phenylcyclohexanone → (4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amine

HRID 2076135노트

반응식

HRID 2076135 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=O>C(O)C>[C:20]1([CH:24]2[C:25]3[N:16]=[C:14]([NH:13][C:10]4[CH:9]=[CH:8][C:7]([C:4]5[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=5)=[CH:12][CH:11]=4)[S:15][C:26]=3[CH2:27][CH2:28][CH2:29]2)[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=1

참가 물질

4

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632614(4-Pyridin-4-yl-phenyl)-thiourea

생성물 1

HCID 44194155(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amine수율 20.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of (4-pyridin-4-yl-phenyl)-thiourea (100 mg, 0.44 mmol) and 2-bromo-6-phenyl-cyclohexanone (116 mg, 0.46 mmol) in ethanol (5 ml) was heated to reflux over night. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as the eluent to yield the title compound (34 mg, 20%) as a yellow solid. MS ISP (m/e): 384.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=8.61 (d, 2H), 7.59 (d, 2H), 7.46 (d, 1H), 7.18-7.33 (m, 5H), 7.13 (d, 2H), 4.08 (m, 1H), 2.75 (m, 2H), 2.18 (m, 1H), 1.7-1.98 (m, 3H).

후처리

  1. temperatureto reflux over night
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-b5c3ab6531d04e63bf00583ca60bc0de
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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