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

HRID 2267002Notes

Reaction equation

HRID 2267002 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([S:16][C:17]3[CH:24]=[CH:23][C:20](C#N)=[CH:19][N: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.[CH2:36]([N:38](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]([S:16][C:17]3[CH:24]=[C:23]([C:36]4[N:31]=[N:32][NH:33][N:38]=4)[CH:20]=[CH:19][N:18]=3)[CH:11]=2)[CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 685360946-(3-((4-Acetyl-3-hydroxy-2-propylphenoxy)methyl)phenylthio) nicotinonitrile

Product 1

HCID 595995721-(2-hydroxy-3-propyl-4-{3-[4-(2H-tetrazol-5-yl)-pyridin-2-ylsulfanyl]-benzyloxy}-phenyl)-ethanone

Procedure

Employing the procedure essentially as described in Example 1 using 6-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-nicotinonitrile (430 mg, 1.03 mmol), sodium azide (668 mg, 10.3 mmol), and triethylamine hydrochloride (1.41 g, 10.3 mmol) purify by reverse phase chromatography eluting with methanol: acetic acid: water, the title compound is obtained as a white solid (77 mg, 16%): 1H NMR (CD3CN) δ 0.83 (t, 3H), 1.48 (sextuplet, 2H), 2.53 (s, 3H), 2.60 (t, 2H), 5.24 (s, 2H), 6.62 (d, 1H), 7.11 (d, 1H), 7.56 (m, 3H), 7.71 (m, 2H), 8.11 (dd, 1H), 8.96 (dd, 1H), 12.82 (bs, 1H); MS (esi negative) m/z 460 (m−1).

Workup

  1. custompurify by reverse phase chromatography
  2. washeluting with methanol

Sources & evidence

ORD record
ord-11eff380a6d94ac58760e59df3f94538
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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