2-Methylquinoline-4-carbaldehyde → (Z)-5-((6-methoxy-2-(4-((((2-methylquinolin-4-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione

HRID 1397008Notes

Reaction equation

HRID 1397008 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[C:13](/[CH:15]=[C:16]3/[C:17](=[O:22])[NH:18][C:19](=[O:21])[S:20]/3)[CH:12]=[C:11]([O:23][CH3:24])[N:10]=2)[CH2:5][CH2:4]1.[CH3:25][C:26]1[CH:35]=[C:34]([CH:36]=O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1>>[CH3:24][O:23][C:11]1[N:10]=[C:9]([N:6]2[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][CH2:36][C:34]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:25])[CH:35]=3)[CH2:4][CH2:5]2)[N:14]=[C:13](/[CH:15]=[C:16]2/[C:17](=[O:22])[NH:18][C:19](=[O:21])[S:20]/2)[CH:12]=1

Participants

3

Reactant 2

HCID 135668342-Methylquinoline-4-carbaldehydeHCID 53251145(Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Product 1

HCID 66571261(Z)-5-((6-methoxy-2-(4-((((2-methylquinolin-4-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Procedure

(Z)-5-((6-methoxy-2-(4-((((2-methylquinolin-4-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione was prepared using (Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione (Example 153), the general reductive amination procedure and 2-methylquinoline-4-carbaldehyde (45.8 mg, 63 mg theoretical, 72.2%). LC-MS m/z 505 (M+1).

Sources & evidence

ORD record
ord-453f39b3ab7246579f812ae1b38ced76
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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