2-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide → N-(5-chloropyridin-2-yl)-5-fluoro-2-(piperidin-4-ylmethyl)aminobenzamide

HRID 1247063Notes

Reaction equation

HRID 1247063 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18](=[O:19])[C:17]2[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:16]=2[NH:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:22][CH:23]=1

Participants

3

Reactant 1

HCID 219066432-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide

Product 1

HCID 21906364N-(5-chloropyridin-2-yl)-5-fluoro-2-(piperidin-4-ylmethyl)aminobenzamideYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(1-Boc-piperidin-4-ylmethylamino)-N-(5-chloropyridin-2-yl)-5-fluorobenzamide from above (5.8 g, 12 mmol) in trifluoroacetic acid (125 mL) was heated at 70° C. for 2 h, then at room temperature for 24 h. The solvent was removed in vacuo; then the residue was directly applied to a silica gel column. Elution with dichloromethane-2 M ammonia in methanol (9:1) afforded 3.8 g (84%) of the title compound as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. washElution with dichloromethane-2 M ammonia in methanol (9:1)

Sources & evidence

ORD record
ord-fd2ac867db8649cbaec6b2ed35423ae0
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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