Methyl 3-(3,5-dimethyl-4-formylphenyl)propionate → 3-{4-[6-(3,4-Dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

HRID 1514988Notes

Reaction equation

HRID 1514988 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:20][O:21][C:22](=[O:35])[CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH:32]=O)=[C:27]([CH3:34])[CH:26]=1>>[CH3:20][O:21][C:22](=[O:35])[CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([C:32]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=4)[CH:16]=[CH:17][C:18]=3[N:19]=2)=[C:27]([CH3:34])[CH:26]=1

Participants

3

Reactant 2

HCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionateHCID 66965643HCID 66965643, compound

Product 1

HCID 669655423-{4-[6-(3,4-Dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

Procedure

The title compound was prepared from 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide and 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester (from Example 6-17) analogous to Example 6-1. 1H NMR (Methanol-d4, 400 MHz): δ 8.32 (d, 1H), 7.91 (d, 1H), 7.79 (dd, 1H), 7.48 (s, 1H), 7.45 (dd, 1H), 7.15 (d, 1H), 7.08 (s, 2H), 3.67 (s, 3H), 2.97 (t, 2H), 2.71 (t, 2H), 2.30 (s, 3H), 2.27 (s, 3H), 2.15 (s, 6H). MS (m/z) 456.1 (M+1); Retention time: 1.44 min (Method 10).

Sources & evidence

ORD record
ord-70fa5c9bf50b43d293840a00b2b91bdb
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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