2-methyl-2H-1,2,3,4-tetrazol-5-amine → [2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine

HRID 2075072

Reaktionsgleichung

Reaktionsgleichung von HRID 2075072
[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2[CH:10]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][N:23]1[N:27]=[N:26][C:25]([NH2:28])=[N:24]1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2[CH2:10][NH:28][C:25]2[N:26]=[N:27][N:23]([CH3:22])[N:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 4311764Sodium borohydrideHCID 589686992-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 58968679[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzaldehyde (90 mg, 0.30 mmol) and 2-methyl-2H-tetrazol-5-amine (35.6 mg, 0.36 mol) in toluene (1.5 ml) was heated at 50° C. for overnight. Solvent was removed in vacuo and reaction mixture was diluted with ethanol (2 ml) and treated with sodium borohydride (21.8 mg, 0.577 mmol) and stirred at room temperature for overnight. Reaction mixture was concentrated in vacuo and diluted with ethyl acetate (100 ml) and washed with water (30 ml). Organic layer was dried over anhydrous magnesium sulphate and concentrated in vacuo. The crude product was purified on Biotage column (12+M), eluting with 7% ethyl acetate in heptane (1 CV), 7-60% (10CV), 60% (2CV) to yield the title compound (65 mg, 58%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.1 (m, 4H) 1.25 (s, 2H) 1.62 (m, 3H) 1.76 (m, 1H) 1.99 (d, J=14.1 Hz, 1H) 3.16 (s, 3H) 4.13 (s, 3H) 4.2 (d, J=7.5 Hz, 1H) 4.48 (dd, J=5.4 Hz, 1H) 4.65 (dd, J=6.6 Hz, 1H) 4.93 (m, 1H) 7.47 (d, J=7.8 Hz, 1H) 7.54 (d, J=8.3 Hz, 1H) 7.67 (s, 1H). MS (ES+) Calc: 383.4, Found: 349.3 (M−34).

Aufarbeitung

  1. customSolvent was removed in vacuo and reaction mixture
  2. additionwas diluted with ethanol (2 ml)
  3. customReaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with ethyl acetate (100 ml)
  6. washwashed with water (30 ml)
  7. dry with materialOrganic layer was dried over anhydrous magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on Biotage column (12+M)
  10. washeluting with 7% ethyl acetate in heptane (1 CV), 7-60% (10CV), 60% (2CV)

Quellen und Nachweise

ORD-Eintrag
ord-ac28c118592f48129bf3ef568b7c5d61
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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