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

HRID 1247086Notes

Reaction equation

HRID 1247086 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:25])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:6][CH:7]=1.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:22]2[CH2:21][CH2:20][CH:19]([CH2:18][NH:17][C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:25])[CH2:24][CH2:23]2)[CH:32]=[CH:31][N:30]=1)([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 21906364N-(5-chloropyridin-2-yl)-5-fluoro-2-(piperidin-4-ylmethyl)aminobenzamide

Product 1

HCID 219065632-[1-(2-Carboxypyridin-4-yl)piperidin-4-ylmethylamino]-N-(5-chloropyridin-2-yl)-5-fluorobenzamideYield 45.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a similar procedure to that described in Example 52, N-(5-chloropyridin-2-yl)-5-fluoro-2-(piperidin-4-ylmethyl)aminobenzamide (200 mg, 0.55 mmol), 4-chloropicolinic acid (130 mg, 0.83 mmol), triethylamine (111 mg, 1.10 mmol), and ethanol (4 mL) yielded 120 mg (45%) of the title compound.

Sources & evidence

ORD record
ord-0a290f7fbbcb4fa9be84df6a1dc8b38c
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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