6-(3-Thienyl)pyridine-2-carboxaldehyde → (Z)-5-((6-methoxy-2-(4-((((6-(thiophen-3-yl)pyridin-2-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione

HRID 1397007Notes

Reaction equation

HRID 1397007 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.[S:25]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[C:34]([CH:36]=O)[CH:33]=[CH:32][CH:31]=2)=[CH:26]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[CH:33]=[CH:32][CH:31]=[C:30]([C:27]4[CH:28]=[CH:29][S:25][CH:26]=4)[N: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 162178896-(3-Thienyl)pyridine-2-carboxaldehydeHCID 53251145(Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Product 1

HCID 86672839(Z)-5-((6-methoxy-2-(4-((((6-(thiophen-3-yl)pyridin-2-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Procedure

(Z)-5-((6-methoxy-2-(4-((((6-(thiophen-3-yl)pyridin-2-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 6-(thiophen-3-yl)picolinaldehyde (34.3 mg, 65 mg theoretical, 52.8%). LC-MS m/z 523 (M+1).

Sources & evidence

ORD record
ord-06c0ccd808b7425db09a54640ff4b7dc
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

Loading…