4-Methylbenzaldehyde → HCID 178490782, compound

HRID 1297188Notes

Reaction equation

HRID 1297188 reaction equation
C1(C)C=CC(C=O)=CC=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[NH:29][C:28]4[CH:30]=[CH:31][C:32]([C:34]([NH2:36])=[O:35])=[CH:33][C:27]=4[N:26]=3)=[CH:21][CH:20]=2)[CH2:12][CH2:11]1.N1CCCCC1C[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2NC3C=CC(C(N)=O)=CC=3N=2)=[CH:48][CH:47]=1>>[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]4[NH:29][C:28]5[CH:30]=[CH:31][C:32]([C:34]([NH2:36])=[O:35])=[CH:33][C:27]=5[N:26]=4)=[CH:23][CH:24]=3)[CH2:12][CH2:11]2)=[CH:48][CH:47]=1

Participants

4

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 178513585HCID 178513585, compoundHCID 178513587HCID 178513587, compound

Product 1

HCID 178490782HCID 178490782, compound

Procedure

This compound was prepared using the methods outlined in Example 27, substituting p-anisaldehyde for p-tolualdehyde and 2-[4-(2-piperidin-4-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide for 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide. HPLC (Method C): Rt=4.49. MS (ESI+): mass calcd. for C29H32N4O3, 484.25; m/z found, 485.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.17 (s, 1H), 8.00 (d, J=8.8 Hz, 2H), 7.93 (d, J=8.5 Hz, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.31 (d, J=8.7 Hz, 2H), 7.13 (d, J=8.8 Hz, 2H), 6.92 (d, J=8.7 Hz, 2H), 4.13 (s, 2H), 4.13-4.11 (m, 2H), 3.73 (s, 3H), 3.41-3.38 (m, 2H), 2.94-2.85 (m, 2H), 1.99-1.96 (m, 2H), 1.86-1.79 (m, 1H), 1.79-1.71 (m, 2H), 1.47-1.36 (m, 2H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-93b22dde623e4c409aaeacad32696a4a
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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