3-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ethyl}-benzonitrile → 1-[2-hydroxy-3-propyl-4-(4-{1-[3-(1H-tetrazol-5-yl)-phenyl]-ethyl}-benzyloxy)-phenyl]-ethanone

HRID 1818519Notes

Reaction equation

HRID 1818519 reaction equation
F[CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:25]=1)[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[CH2:19][CH2:20][CH3:21])=[CH:5][CH:4]=1.[C:35](C1C=CC(OCC2C=CC(C(C3C=C(C=CC=3)C#N)C)=CC=2)=C(CCC)C=1O)(=O)C>>[OH:18][C:11]1[C:10]([CH2:19][CH2:20][CH3:21])=[C:9]([O:8][CH2:7][C:6]2[CH:22]=[CH:23][C:3]([CH:2]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:34][N:33]=[N:32][N:31]=4)[CH:25]=3)[CH3:35])=[CH:4][CH:5]=2)[CH:14]=[CH:13][C:12]=1[C:15](=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 666995733-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ethyl}-benzonitrileHCID 1784396501-[4-(4-{fluoro-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

Product 1

HCID 1784396491-[2-hydroxy-3-propyl-4-(4-{1-[3-(1H-tetrazol-5-yl)-phenyl]-ethyl}-benzyloxy)-phenyl]-ethanone

Procedure

The title compound is prepared essentially as described for 1-[4-(4-{fluoro-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone employing 3-{1-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ethyl}-benzonitrile. The title compound is obtained (12.5 mg, 45%) as a white solid. 1H NMR (DMSO-d6) δ 12.85 (s, 1H), 8.00 (s, 1H), 7.75-7.85 (m, 2H), 7.35-7.54 (m, 6H), 6.73 (d, 1H), 5.23 (s, 2H), 4.32 (m, 1H), 2.55-2.60 (m, 5H), 1.66 (d, 3H), 1.46-1.50 (m, 2H), 0.87 (t, 3H). LCMS M+1 457.

Workup

  1. customThe title compound is prepared essentially

Sources & evidence

ORD record
ord-e12a0c10068b4d33ba78bdfda7397708
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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