Trifluoroacetic acid → HCID 57671538, compound

HRID 1801990Notes

Reaction equation

HRID 1801990 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([NH:12][CH3:13])=[CH:10][N:11]=1)[C:5]([O:7]C)=O.[C:14]([O:18][C:19]([C:21]1[C:26](C(OC)=O)=CC(Cl)=NC=1)=[O:20])(C)(C)C.C(O)(C(F)(F)F)=[O:33]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:12]([CH3:13])[C:26](=[O:33])[C:21]([C:19]([O:18][CH3:14])=[O:20])=[C:5]2[OH:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 57671617HCID 57671617, compoundHCID 86631269HCID 86631269, compound

Product 1

HCID 57671538HCID 57671538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-chloro-5-(methylamino)isonicotinate. To a solution of methyl 5-(tert-butoxycarbonyl)-2-chloroisonicotinate (0.5 g, 1.7 mmol) in dry DCM (10 mL) was added TFA (4.4 mL) with stirring and cooling using an ice-bath. The mixture was stirred at room temperature for 2 hours and then evaporated under reduced pressure. The residue was dissolved in water, and the solution was adjusted to pH=8 by treatment with saturated NaHCO3. The mixture was extracted twice with EtOAc. The combined organic layers were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue was dried in vacuo to give the title compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionThe mixture was extracted twice with EtOAc
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-f27b3c908d9f455395190c591d0e0a4c
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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