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

HRID 2267039Notes

Reaction equation

[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]

Participants

Reactant 3

HCID 11130Triethylamine hydrochloride

HCID 33557Sodium Azide

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

Product 1

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

Procedure

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).

Sources & evidence

ORD record: ord-ba3baab2ac7949fda34d56b139ceed24
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858646B2

Reaction notes

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