4-Methylbenzaldehyde → HCID 178513584, compound

HRID 1297191Notes

Reaction equation

HRID 1297191 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]1[CH:30]=C(C=C[C:36]=1[Cl:37])C=O.[C:38]1(C)[CH:43]=CC(C=O)=C[CH:39]=1>>[Cl:28][C:29]1[CH:30]=[C:5]([CH:4]=[CH:3][C:36]=1[Cl:37])[CH2:6][N:1]1[CH2:43][CH2:38][CH2:39][CH:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=4[N:17]=3)=[CH:14][CH:15]=2)[CH2:2]1

Participants

4

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 227103,4-DichlorobenzaldehydeHCID 178513585HCID 178513585, compound

Product 1

HCID 178513584HCID 178513584, 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 3,4-dichlorobenzaldehyde for p-tolualdehyde. HPLC (Method C): Rt=4.79. MS (ESI+): mass calcd. for C27H26Cl2N4O2, 508.14; m/z found, 509.3 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.17 (s, 1H), 8.02 (d, J=9.1 Hz, 2H), 7.92 (dd, J=1.5, 8.7 Hz, 1H), 7.67 (m, 2H), 7.58 (d, J=8.3 Hz, 1H), 7.28 (dd, J=2.0, 8.4 Hz, 1H), 7.13 (d, J=9.1 Hz, 2H), 4.32-4.25 (m, 2H), 4.08-4.05 (m, 1H), 3.98-3.94 (m, 1H), 3.61-3.58 (m, 1H), 3.45-3.41 (m, 1H), 2.92-2.87 (m, 2H), 2.36-2.25 (m, 1H), 2.00-1.90 (m, 2H), 1.81-1.71 (m, 1H), 1.46-1.36 (m, 1H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-833387c0a5d5479e95750bf426706c7f
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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