Triethylamine → 2-[1-(2-Carboxypyridin-4-yl)piperidin-4-ylmethylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 1247083Notes

Reaction equation

HRID 1247083 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].Cl[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]([OH:35])=[O:34])[CH:28]=1.C(N(CC)CC)C>C(O)C>[C:33]([C:29]1[CH:28]=[C:27]([N:23]2[CH2:22][CH2:21][CH:20]([CH2:19][NH:18][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:6]=3[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=3)=[O:8])[CH2:25][CH2:24]2)[CH:32]=[CH:31][N:30]=1)([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 98861065-chloro-N-(5-chloropyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide

Product 1

HCID 219065042-[1-(2-Carboxypyridin-4-yl)piperidin-4-ylmethylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a similar procedure to that described in Example 52, 5-chloro-N-(5-chloropyridin-2-yl)-2-(piperidin-4-ylmethyl)aminobenzamide (166 mg, 0.44 mmol), 4-chloropicolinic acid (103 mg, 0.66 mmol), triethylamine (89 mg, 0.88 mmol, and ethanol (3 mL) yielded 180 mg (82%) of the title compound.

Sources & evidence

ORD record
ord-fc807513e3ec4f45b7aaf92c0fdbd256
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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