2-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide → 2-[4-(tert-Butyl)-2-(piperidin-4-yloxy)benzoylamino]-4-chloro-N-(5-chloro-pyridin-2-yl)benzamide hydrochloride

HRID 644184Notes

Reaction equation

HRID 644184 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:10])=[C:7]([O:31][CH:32]2[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>Cl.O1CCOCC1>[ClH:23].[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:10])=[C:7]([O:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 685368592-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide

Product 1

HCID 685356032-[4-(tert-Butyl)-2-(piperidin-4-yloxy)benzoylamino]-4-chloro-N-(5-chloro-pyridin-2-yl)benzamide hydrochlorideYield 46.7%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

2-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide (0.4 g, 0.64 mmol) was dissolved in 4 N HCl/p-dioxane (15 mL). After stirring for 30 min, the solution was concentrated in vacuo and the residue was purified by RPHPLC, eluting with a gradient of 20% through 60% acetonitrile in 0.05% aq HCl over 320 min. The clean product containing fractions were combined, partially concentrated and lypholyzed to give 0.0864 g (23%) of white solid.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe residue was purified by RPHPLC
  3. washeluting with a gradient of 20% through 60% acetonitrile in 0.05% aq HCl over 320 min
  4. additionThe clean product containing fractions
  5. concentrationpartially concentrated

Sources & evidence

ORD record
ord-3633d7d9aee0424e811f60bf1970bb0a
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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