3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide → N-(5-Chloropyridin-2-yl)-3-[4-(methylthio)-2-(piperidin-4-yloxy)benzoylamino]pyridine-2-carboxamide

HRID 1434829Notes

Reaction equation

HRID 1434829 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40][CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:26]([C:21]2[C:20]([NH:19][C:17](=[O:18])[C:16]3[CH:36]=[CH:37][C:38]([S:40][CH3:41])=[CH:39][C:15]=3[O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:27])=[N:30][CH:31]=1

Participants

3

Reactant 1

HCID 116999433-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

Product 1

HCID 11620252N-(5-Chloropyridin-2-yl)-3-[4-(methylthio)-2-(piperidin-4-yloxy)benzoylamino]pyridine-2-carboxamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The 3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (184 mg, 0.31 mmol) was dissolved in TFA (4 mL). After 5 minutes, the reaction was concentrated in vacuo. The residue was diluted with dichloromethane (100 mL) and extracted with saturated aqueous sodium carbonate (2×10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give the desired product as a white solid (139 mg, 0.28 mmol, 90%).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane (100 mL)
  3. extractionextracted with saturated aqueous sodium carbonate (2×10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac5aefc44d0b42dbae914d99e4841b84
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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