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

HRID 1882981Notes

Reaction equation

HRID 1882981 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.Cl[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C(O)C>[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[CH2:20][CH2:21][N:22]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH2:23][CH2:24]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 21906364N-(5-chloropyridin-2-yl)-5-fluoro-2-(piperidin-4-ylmethyl)aminobenzamide

Product 1

HCID 21906493N-(5-chloropyridin-2-yl)-5-fluoro-2-[1-(4-pyridinyl)piperidin-4-ylmethylamino]benzamideYield 24%

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 (343 mg, 0.95 mmol), 4-chloropyridine hydrochloride (709 mg, 4.73 mmol), triethylamine (479 mg, 4.73 mmol), and ethanol (3 mL) yielded 100 mg (24%) of the title compound.

Sources & evidence

ORD record
ord-54a0ba1e7eea426da2660d4fb1b7dc04
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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