3-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-vinyl}-benzonitrile → HCID 178436441, compound

HRID 1818517Notes

Reaction equation

HRID 1818517 reaction equation
FC(C1C=CC=C(C2N[N:33]=[N:32][N:31]=2)C=1)C1C=CC(COC2C=CC(C(=O)C)=C(O)C=2CCC)=CC=1.[C:35]([C:38]1[CH:61]=[CH:60][C:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]([C:52]3[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=3)[C:55]#[N:56])=[CH2:51])=[CH:46][CH:45]=2)=[C:40]([CH2:62][CH2:63][CH3:64])[C:39]=1[OH:65])(=[O:37])[CH3:36]>>[OH:65][C:39]1[C:40]([CH2:62][CH2:63][CH3:64])=[C:41]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([C:50]([C:52]3[CH:59]=[CH:58][CH:57]=[C:54]([C:55]4[NH:33][N:32]=[N:31][N:56]=4)[CH:53]=3)=[CH2:51])=[CH:48][CH:49]=2)[CH:60]=[CH:61][C:38]=1[C:35](=[O:37])[CH3:36]

Participants

3

Reactant 2

HCID 666996573-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-vinyl}-benzonitrileHCID 1784396501-[4-(4-{fluoro-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

Product 1

HCID 178436441HCID 178436441, compoundYield 65%

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]-vinyl}-benzonitrile to give 72 mg, of the title compound as a tan solid 65%. 1H NMR (CDCl3) δ 12.87 (s, 1H), 8.00-8.07 (m, 2H), 7.83-7.86 (m, 2H), 7.65 (t, 1H), 7.39-7.54 (m, 4H), 6.76 (d, 1H), 5.68 (s, 1H), 5.63 (s, 1H), 5.32 (s, 2H), 2.58-2.65 (m, 5H), 1.48-1.53 (m, 2H), 0.89 (t, 3H). LCMS M−1 453.

Workup

  1. customThe title compound is prepared essentially
  2. customto give 72 mg

Sources & evidence

ORD record
ord-a72bcb9475e74d949c3c0881158a16f1
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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