1-(Bromomethyl)-4-(trifluoromethoxy)benzene → cis-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethoxy-benzyl)-amino]-cyclohexanecarboxylic acid amide

HRID 7036

反応式

HRID 7036 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH2:20])=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:31])([F:32])[F:33])=[CH:25][CH:24]=2)[C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH2:20])=[O:19])(=[O:9])=[O:10])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 69655699cis-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

生成物 1

HCID 69655582cis-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethoxy-benzyl)-amino]-cyclohexanecarboxylic acid amide収率 67%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

cis-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid amide (200 mg, 0.63 mmol), CsCO3 (250 mg, 0.76 mmol), and 1-bromomethyl-4-trifluoromethoxy-benzene (155 mg, 0.69 mmol) was stirred in acetonitrile (15 mL) at room temperature for 18 h. The reaction was then diluted with EtOAc (150 mL) and washed with H2O, brine, dried over Na2SO4 and concentrated to give a crude white wax. Further purification by flash chromatography (silica gel, 0.5%–1% MeOH/CHCl3) afforded the titled compound (205 mg) as a white solid in 67% yield: 1H NMR (DMSO-d6) δ 7.75 (d, 2 H, J=8.0 Hz), 7.59 (d, 2 H, J=8.0 Hz), 7.36 (m, 3 H), 7.21 (d, 2 H, J=8.0 Hz), 6.69 (s br, 1 H), 4.58 (AB2, 2 H, Δv=17, Jab=64 Hz), 3.89 (m, 1 H), 2.79 (s, 1 H), 2.44 (m, 1 H), 1.78 (m, 1 H), 1.66 (m, 2 H), 1.31 (m, 3 H), 0.98 (m, 1 H); MS m/e 491.03 (M+H)+.

後処理

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a crude white wax
  5. customFurther purification by flash chromatography (silica gel, 0.5%–1% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-ed10b2c70d2b47c3a62ee8f7be7d71c0
出典データセット
uspto-grants-2006_08
特許番号
US07084178B2

関連ノート

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