Ethanol → N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine

HRID 2075080

反応式

HRID 2075080 の反応式
[CH3:1][O:2][C:3]1([C:10]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=2[CH:12]=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:22][N:23]1[N:27]=[N:26][C:25]([NH2:28])=[N:24]1.C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1([C:10]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=2[CH2:12][NH:28][C:25]2[N:26]=[N:27][N:23]([CH3:22])[N:24]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 702EthanolHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 4311764Sodium borohydrideHCID 589686662-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde

生成物 1

HCID 58968736N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine収率 55.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde (118 mg, 0.393 mmol) and 2-methyl-2H-tetrazol-5-amine (148 mg, 1.49 mmol) in toluene (3 mL) was heated at reflux for 16 hours, after which solvent was removed to give a gummy solid. Ethanol (3 mL) and sodium borohydride (25 mg; 0.660 mmol) were added to the residue. The resulting mixture was stirred at room temperature for 16 hours. Solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate and washed twice with water and dried over sodium sulfate and concentrated under reduced pressure. The crude was purified over 4 g RediSep (eluted with 20-60% ethyl acetate in heptane) to give 83 mg (55% yield) of title compound. MS (ES+): Calc: 383.4, Found: 352.3 (M-OMe). 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (s, 1H), 7.48 (dd, J=8.77 Hz, 1H), 7.42 (d, J=8.30 Hz, 1H), 4.92 (d, J=6.22 Hz, 2H), 4.75 (t, J=6.22 Hz, 1H), 4.16 (s, 3H), 3.03 (s, 3H), 2.26 (m, 2H), 2.07 (m, 2H), 1.88-1.77 (m, 2H), 1.75-1.65 (m, 2H), 1.64-1.52 (m, 4H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customafter which solvent was removed
  4. customto give a gummy solid
  5. customSolvent was evaporated under reduced pressure
  6. washwashed twice with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was purified over 4 g RediSep (eluted with 20-60% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-8414bfe90faf4f0f9317391bee544676
出典データセット
uspto-grants-2011_04
特許番号
US07919506B2

関連ノート

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