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

反応式

[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:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[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][C:20]([C:21]4[N:31]=[N:32][NH:33][N:22]=4)=[CH:19][CH:18]=3)[CH:11]=2)[CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2]

参加物

反応物 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

HCID 685330004-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzonitrile

生成物 1

HCID 595995961-(2-hydroxy-3-propyl-4-{3-[4-(2H-tetrazol-5-yl)-phenylamino]-benzyloxy}-phenyl)-ethanone収率 29%

実験手順

Using the general procedure for formation of tetrazole (Et3NHCl method) of Example 1 using 4-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzonitrile (380 mg, 0.949 mmol), sodium azide (308 mg, 4.74 mmol), and triethylamine hydrochloride (653 mg, 4.74 mmol) to yield the title product as a white solid (120 mg, 29%): 1H NMR (DMSO-d6) δ 0.785 (t, 3H), 1.44 (sextuplet, 2H), 2.52 (s, 3H), 2.55 (t, 2H), 5.20 (s, 2H), 6.68 (d, 1H), 6.97 (d, 1H), 7.04 (d, 1H), 7.15 (d, 2H), 7.24 (s, 1H), 7.29 (t, 1H), 7.76 (d, 1H), 7.82 (d, 2H), 8.69 (s, 1H), 12.80 (s, 1H); MS (esi negative) m/z (rel intensity) 442 (100).