HCID 68209165, compound → HCID 68209208, compound

HRID 2202814Notes

Reaction equation

HRID 2202814 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([OH:23])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH2:21][CH3:22])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:20][C:19]1[C:14]([C:11]2([OH:23])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:15][C:16]([CH2:21][CH3:22])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 68209165HCID 68209165, compound

Product 1

HCID 68209208HCID 68209208, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-Chloro-6-ethyl-4′-hydroxy-3′,4′,5′,6′-tetrahydro-2′H[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.086 g, 0.25 mmol) was dissolved in TFA (1 mL) and DCM (1 mL). The mixture was stirred for 20 minutes and the solvent removed by evaporation under vacuum and the residues were passed through an SCX cartridge, eluting with 2 M ammonia in methanol to give the title compound (0.052 g). LCMS m/z 243.25 [M+H]+. R.T.=2.45 min (Analytical Method 3).

Workup

  1. customthe solvent removed by evaporation under vacuum
  2. washeluting with 2 M ammonia in methanol

Sources & evidence

ORD record
ord-ad1177636cf64de4ac5b8e66fe4b66c3
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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