Water → HCID 59543403, compound

HRID 1798938Notes

Reaction equation

HRID 1798938 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O.[OH-].[Na+]>C(Cl)Cl>[N:26]1([C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:18]=[CH:19][C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[N:15][CH:16]=3)=[CH:21][CH:22]=2)[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59543413HCID 59543413, compound

Product 1

HCID 59543403HCID 59543403, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Morpholin-4-ylphenyl)-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.37 g, 0.874 mmol) was dissolved in DCM (12 mL), TFA (4 mL) was added and the reaction mixture was stirred at RT for 1 hour, until all starting material had disappeared. Water and 1 N NaOH was added until pH=12. After extraction with DCM (4×40 mL) the DCM phase was dried with Na2CO3, filtered and evaporated to give 280 mg (100%) white crystals.

Workup

  1. extractionAfter extraction with DCM (4×40 mL) the DCM phase
  2. dry with materialwas dried with Na2CO3
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-821a6d83311446898743eebd9995f7d3
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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