Sodium methanethiolate → (3,5-Bis-trifluoromethyl-benzyl)-[2-(cyclohexyl-methylsulfanyl-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine

HRID 2075083ノート

反応式

HRID 2075083 の反応式
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25](Br)[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH3:42][S-:43].[Na+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[S:43][CH3:42])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

参加物

5

反応物 2

HCID 4378561Sodium methanethiolateHCID 58968654(3,5-Bis-trifluoromethyl-benzyl)-[2-(bromo-cyclohexyl-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine

生成物 1

HCID 58968696(3,5-Bis-trifluoromethyl-benzyl)-[2-(cyclohexyl-methylsulfanyl-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine収率 94.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (3,5-bis-trifluoromethyl-benzyl)-[2-(bromo-cyclohexyl-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine (26 mg; 0.039 mmol) in THF (1 mL) was added sodium thiomethoxide (8 mg; 0.114 mmol). Reaction stirred at room temperature for 16 hours. Reaction was diluted with ethyl acetate and washed twice with water. The organic layer was dried sodium sulfate and concentrated to give 23 mg (93% yield) of the title compound as a gum. MS (ES+): Calc: 625.6, Found: 626.0 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (s, 1H), 7.67 (s, 2H), 7.57 (d, J=7.88 Hz, 1H), 7.75-7.56 (bs, 1H), 7.27 (s, 1H), 4.79 (t, J=15.35 Hz, 2H), 4.69 (t, J=15.77 Hz, 2H), 4.23 (s, 3H), 3.81 (bs, 1H), 2.21 (d, J=12.86 Hz, 1H), 1.76 (s, 3H), 1.76-1.57 (m, 4H), 1.36 (d, J=12.45 Hz, 1H), 1.25-1.03 (m, 3H), 1.0-0.76 (m, 2H).

後処理

  1. customReaction
  2. customReaction
  3. washwashed twice with water
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-71f1c1188fe9441da9932b36cdc5bdd6
出典データセット
uspto-grants-2011_04
特許番号
US07919506B2

反応ノート

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