Sodium Hydroxide → 2-[4-(tert-Butyl)-2-(piperidin-4-yloxy)benzylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 644207Notes

Reaction equation

HRID 644207 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][NH:10][C:11]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[C:7]([O:30][CH:31]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][NH:10][C:11]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[C:7]([O:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 685338362-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 578607902-[4-(tert-Butyl)-2-(piperidin-4-yloxy)benzylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the 2-[4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide (0.2 g, 0.32 mmol) in trifluoroacetic acid (5 mL) was stirred at room temperature for 2 h. The mixture was poured into ice, then taken to basic pH with 5 N aqueous sodium hydroxide, and extracted with dichloromethane. The organic layer was separated, and the aqueous layer was thoroughly extracted with dichloromethane. The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to a yellow oily residue which was purified on a silica gel chromatotron plate. Elution with 9:1 dichloromethane-2 N ammonia in methanol provided the title compound as a clear oil which foamed up under vacuum (0.15 mg, 87%). Recrystallization of the oil from ethyl acetate-hexanes provided analytically pure product (0.09 mg) as a yellow-white crystalline solid.

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was thoroughly extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow oily residue which
  8. customwas purified on a silica gel chromatotron plate
  9. washElution with 9:1 dichloromethane-2 N ammonia in methanol

Sources & evidence

ORD record
ord-c751cd35b799495db4d8728098656538
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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