Trifluoroacetic acid → HCID 57602493, compound

HRID 1787943Notes

Reaction equation

HRID 1787943 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18](=[O:35])[C:19]3[CH:24]=[CH:23][C:22]([C:25]4([CH3:30])OCC[O:26]4)=[CH:21][C:20]=3[O:31]COC)=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:18]([NH:17][C:16]2[C:11]([C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:35])=[C:20]([OH:31])[CH:21]=1)(=[O:26])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57602476HCID 57602476, compound

Product 1

HCID 57602493HCID 57602493, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(5-Chloropyridin-2-yl)-3-[4-(2-methyl-1,3-dioxolan-2-yl)-2-(methoxymethoxy)benzoylamino]pyridine-2-carboxamide (3.10 g) is treated with a solution of TFA (20 mL) and water (20 mL) for 2 h before the solution is evaporated. The residue is slurried with ethyl acetate to provide a solid which is collected and washed. The solid is dispersed in ethyl acetate and extracted with a mixture of aqueous potassium carbonate and 1 N NaOH. The resulting organic phase is washed with very dilute HCl, dried and evaporated to afford the product as a solid (0.476 g), which is used directly without further purification.

Workup

  1. customis evaporated
  2. customto provide a solid which
  3. customis collected
  4. washwashed
  5. additionThe solid is dispersed in ethyl acetate
  6. extractionextracted with a mixture of aqueous potassium carbonate and 1 N NaOH
  7. washThe resulting organic phase is washed with very dilute HCl
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-506d020f05dc4e06926c5a703d23fbaa
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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