Benzaldehyde → HCID 178461201, compound

HRID 81222Notes

Reaction equation

HRID 81222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:17][C@H:18]4[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]4)[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([C:25]#[N:26])[N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:17][C@H:18]4[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]4)[C:15]([CH:27]([OH:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:16][C:12]=3[CH:11]=[C:10]([C:25]#[N:26])[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 178461253HCID 178461253, compound

Product 1

HCID 178461201HCID 178461201, compound

Procedure

4-(5-chloropyridin-3-yl)-2-(hydroxy(phenyl)methyl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile was prepared using 4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (product of Step 2, Preparative Example 3.1) and benzaldehyde in a manner analogous to Example 6.1, Step 1. 1H NMR (600 MHz, CD3OD) δ 8.75 (d, J=2.2, 1H), 8.69 (s, 1H), 8.26 (s, 1H), 8.21 (s, 1H), 7.48 (d, J=7.5, 2H), 7.37 (t, J=7.5, 2H), 7.34-7.28 (m, 1H), 6.22 (s, 1H), 3.94 (s, 2H), 1.40 (t, J=14.0, 2H), 1.06-0.98 (m, 1H), 0.83-0.77 (m, 1H), 0.75-0.68 (m, 5H), 0.64-0.56 (m, 1H), 0.51-0.36 (m, 3H). MS ESI calc'd. for C27H26ClN5O [M+H]+ 472. found 472.

Sources & evidence

ORD record
ord-9af46d8d9f774c168d4beea04bbe2bab
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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