6-Fluoropyridine-2-carboxaldehyde → (Z)-5-((2-(4-((((6-fluoropyridin-2-yl)methyl)amino)methyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione

HRID 1397009Notes

Reaction equation

HRID 1397009 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.[F:25][C:26]1[N:31]=[C:30]([CH:32]=O)[CH:29]=[CH:28][CH:27]=1>>[F:25][C:26]1[N:31]=[C:30]([CH2:32][NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]3[N:14]=[C:13](/[CH:15]=[C:16]4/[C:17](=[O:22])[NH:18][C:19](=[O:21])[S:20]/4)[CH:12]=[C:11]([O:23][CH3:24])[N:10]=3)[CH2:5][CH2:4]2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 106067416-Fluoropyridine-2-carboxaldehydeHCID 53251145(Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Product 1

HCID 66571263(Z)-5-((2-(4-((((6-fluoropyridin-2-yl)methyl)amino)methyl)piperidin-1-yl)-6-methoxypyrimidin-4-yl)methylene)thiazolidine-2,4-dione

Procedure

(Z)-5-((2-(4-((((6-fluoropyridin-2-yl)methyl)amino)methyl)piperidin-1-yl)-6-methoxypyrimidin-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-fluoropicolinaldehyde (26.1 mg, 59 mg theoretical, 43.9%). LC-MS m/z 459 (M+1).

Sources & evidence

ORD record
ord-33f38afedbe742cf8771b3f8aee7a062
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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