4-Methylbenzaldehyde → HCID 178513583, compound

HRID 1297190Notes

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.[Cl:28][C:29]1C=CC(C=O)=[CH:31][CH:30]=1.[C:37]1(C)[CH:42]=CC(C=O)=C[CH:38]=1>>[Cl:28][C:29]1[CH:30]=[CH:31][C:5]([CH2:6][N:1]2[CH2:42][CH2:37][CH2:38][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 77264-Chlorobenzaldehyde

HCID 178513585HCID 178513585, compound

Product 1

HCID 178513583HCID 178513583, 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-chlorobenzaldehyde for p-tolualdehyde. HPLC (Method C): Rt=4.57. MS (ESI+): mass calcd. for C27H27ClN4O2, 474.18; m/z found, 475.3 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.13 (s, 1H), 8.00 (d, J=8.8 Hz, 2H), 7.85 (dd, J=1.5, 8.7 Hz, 1H), 7.63 (d, J=8.5 Hz, 1H), 7.43 (s, 4H), 7.10 (d, J=8.8 Hz, 2H), 4.28-4.27 (m, 2H), 4.08-4.04 (m, 1H), 3.95-3.91 (m, 1H), 3.62-3.57 (m, 1H), 3:45-3.40 (m, 1H), 2.91-2.85 (m, 2H), 2.32-2.24(m, 1H), 2.01-1.89 (m, 2H), 1.80-1.69 (m, 1H), 1.46-1.36 (m, 1H).

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-bd4b9c260149484f9376f145afe886da
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250427B2

Reaction notes

Loading…