Water → N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine

HRID 2075059ノート

反応式

HRID 2075059 の反応式
[CH:1]1([CH:7]([O:37][CH3:38])[C:8]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:9]=2[CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C:12]#[N:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:39]=[N+:40]=[N-:41].[Na+].O>C1(C)C=CC=CC=1>[CH:1]1([CH:7]([O:37][CH3:38])[C:8]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][C:9]=2[CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C:12]2[N:39]=[N:40][NH:41][N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 86615050(2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

生成物 1

HCID 58968733N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine収率 59%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
115 °C

実験手順

To solution of (2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide (144 mg, 0.26 mmol) in toluene was added sodium azide (84.9 mg, 1.31 mmol) followed by TEA-HCl (178.8 mg, 1.3 mmol). The mixture was stirred at 115° C. overnight. Water was added and the mixture was extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+S Biotage silica column (eluted with 5-50% ethyl acetate in heptane) to afford the title compound (90.9 mg, 59%). 1H NMR (400 MHz, CDCl3) δ ppm 0.90-1.16 (m, 5H) 1.23-1.32 (m, 1H) 1.49-1.61 (m, 3H) 1.69 (s, 1H) 1.97 (d, J=12.45 Hz, 1H) 3.21 (s, 3H) 4.05 (d, J=7.88 Hz, 1H) 4.74-4.93 (m, 4H) 7.31 (s, 1H) 7.41 (d, J=7.88 Hz, 1H) 7.52 (d, J=7.88 Hz, 1H) 7.69 (s, 2H) 7.78 (s, 1H). MS (ES+) Calc: 595.2, Found: 596.5 (M+1).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washCombined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography over 25+S Biotage silica column (eluted with 5-50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-7d9dea3483364ca8a4ac50377edb67a0
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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