4-Methylbenzaldehyde → HCID 178513588, compound

HRID 1297187Notes

Reaction equation

HRID 1297187 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4](C=O)=[CH:3][CH:2]=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.N1CCCCC1CCOC1C=CC(C2NC3C=CC(C(N)=O)=CC=3N=2)=CC=1>>[CH2:9]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][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:23][CH:24]=2)[CH2:12][CH2:11]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

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

Product 1

HCID 178513588HCID 178513588, compound

Procedure

This compound was prepared using the methods outlined in Example 27, substituting benzaldehyde 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=4.41. MS (ESI+): mass calcd. for C28H30N4O2, 454.24; m/z found, 455.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.15 (s, 1H), 8.00 (d, J=8.9 Hz, 2H), 7.91 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.40 (br m, 5H), 7.12 (d, J=8.8 Hz, 2H), 4.21 (s, 2H), 4.11 (t, J=6.1 Hz, 2H), 3.43-3.40 (m, 2H), 2.95-2.89 (m, 2H), 2.00-1.97 (m, 2H), 1.87-1.78 (m, 1H), 1.78-1.72 (m, 2H), 1.48-1.37 (m, 2H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a07255e01a0d4d6c9c3bfd7fac2af348
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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