4-Methylbenzaldehyde → HCID 178490781, compound

HRID 1297189Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=3[N:17]=2)=[CH:12][CH:11]=1.C(=O)C1C=C[C:32]([O:35][CH3:36])=[CH:31][CH:30]=1.[C:38]1(C)[CH:43]=CC(C=O)=C[CH:39]=1>>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:5]([CH2:6][N:1]2[CH2:43][CH2:38][CH2:39][CH:7]([CH2:8][O:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[NH:20][C:19]5[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=5[N:17]=4)=[CH:14][CH:15]=3)[CH2:2]2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 77254-Methylbenzaldehyde

HCID 312444-Methoxybenzaldehyde

HCID 178513585HCID 178513585, compound

Product 1

HCID 178490781HCID 178490781, compound

Procedure

This compound was prepared using the methods outlined in Example 27, substituting 2-[4-(piperidin-3-ylmethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide for 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide and p-anisaldehyde for p-tolualdehyde. HPLC (Method C): Rt=4.42. MS (ESI+): mass calcd. for C28H30N4O3, 470.58; m/z found, 471.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.14 (s, 1H), 8.01 (d, J=8.8 Hz, 2H), 7.86 (dd, J=1.5, 8.7 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.34 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.21-4.19 (m, 2H), 4.07-4.04 (m, 1H), 3.95-3.92 (m, 1H), 3.74(s, 3H), 3.61-3.56 (m, 1H), 3.44-3.40 (m, 1H), 2.00-1.89 (m, 2H), 1.79-1.67 (m, 1H), 1.45-1.35 m, 1H).

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-b051197267184698835e31cb9a97a007
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250427B2

Reaction notes

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