4-Acetylbenzoic Acid → VCAM-1 antagonists, AtheroGen

HRID 10682Notes

Reaction equation

HRID 10682 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH:15]=O.[C:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)(=[O:24])[CH3:23]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14](/[CH:15]=[CH:23]/[C:22]([C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)=[O:24])[CH:17]=1

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

Product 1

HCID 10127162VCAM-1 antagonists, AtheroGenYield 66%

Procedure

The title compound was prepared by condensing 5-(1H-indol-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-61A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Red solid, mp 210–212° C., 66% yield. 1H-NMR (Aceton-d6) δ 10.53 (br, s, 1H), 8.32 (s, 1H), 8.14–8.21 (m, 5H), 7.89 (d, J=15 Hz, 1H), 7.52 (d, J=8 Hz, 1H), 7.38 (d, J=7 Hz, 1H), 6.97–7.07 (m, 3H), 6.87 (s, 1H), 4.07 (s, 3H), 4.02 (s, 3H), MS m/z=427 ([M]+). HMRS (EI) calcd. for C26H21NO5: 427.1420; found: 427.1435.

Sources & evidence

ORD record
ord-4ddfaf0a48a44d8bacdcd8eaf156be91
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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