Triethylamine hydrochloride → 1-(2-hydroxy-3-propyl-4-{3-[3-(2H-tetrazol-5-yl)-phenylamino]-benzyloxy}-phenyl)-ethanone

Reaktionsgleichung

[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH:13]=[CH:14][CH:15]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].Cl.C(N(CC)CC)C>>[OH:30][C:5]1[C:6]([CH2:27][CH2:28][CH3:29])=[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]3[CH:24]=[CH:23][CH:22]=[C:19]([C:20]4[N:31]=[N:32][NH:33][N:21]=4)[CH:18]=3)[CH:11]=2)[CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2]

Komponenten

Edukt 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

HCID 685391703-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzonitrile

Produkt 1

HCID 595995081-(2-hydroxy-3-propyl-4-{3-[3-(2H-tetrazol-5-yl)-phenylamino]-benzyloxy}-phenyl)-ethanoneAusbeute 21 %

Versuchsvorschrift

Using the general procedure for formation of tetrazole (Et3NHCl method) of Example 1 using 3-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzonitrile (1.36 g, 3.39 mmol), sodium azide (662 mg, 10.2 mmol), and triethylamine hydrochloride (1.40 g, 10.2 mmol) to yield the title product as a yellow solid (313 mg, 21%): 1H NMR (DMSO-d6) δ 0.791 (t, 3H), 1.43 (sextuplet, 2H), 2.57 (m, 5H), 5.24 (s, 2H), 6.72 (d, 1H), 6.98 (d, 1H), 7.08 (d, 1H), 7.24 (m, 2H), 7.32 (t, 1H), 7.44 (m, 2H), 7.79 (m, 2H), 8.55 (s, 1H), 12.84 (s, 1H); MS (esi negative) m/z (rel intensity) 442 (100).