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

HRID 2075080

반응식

HRID 2075080 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8414bfe90faf4f0f9317391bee544676
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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